Tetrazoyloxime derivative and plant disease control agent

ABSTRACT

According to the present invention, a tetrazoyloxime derivative and a salt thereof, which are excellent in a control effect against plant disease injury, and a plant disease controlling agent containing the same as an active ingredient are provided. The tetrazoyloxime derivative has a structure represented by formula (1) shown below: 
     
       
         
         
             
             
         
       
     
     wherein X represents a halogen atom, etc., n1 represents an integer of 0 to 5, A represents a group represented by formula (2) or (3), and Het represents a group represented by formula (4) or (5): 
     
       
         
         
             
             
         
       
     
     wherein Y represents a C 1-8  alkyl group, R represents a halogen atom, etc., n2 represents an integer of 0 to 3, R 11  represents a halogen atom, etc., and Z or Z 11  represents a group represented by formula: Q 1 C(═O)NH—, etc. (in which Q 1  represents a C 2-8  haloalkenyl group, etc.) (depends on the kind of R or R 11 ).

TECHNICAL FIELD

The present invention relates to a novel tetrazoyloxime derivative, and a plant disease control agent containing the same as an active ingredient.

This application claims priority on Japanese Patent Application No. 2007-206297 filed on Aug. 8, 2007, the disclosure of which is incorporated by reference herein.

BACKGROUND ART

In the cultivation of agricultural and horticultural crops, a large number of controlling agents have been used against crop injury. However, many of them are hardly satisfactory as controlling agents because of insufficient control efficacy, restrictions on their use due to appearance of pathogenic fungi having drug resistance, phytotoxicity or pollution on plants, or strong toxicity on humans, domestic animals and fishes. Therefore, there has been required to develop plant disease controlling agents applicable safely and having less of the drawbacks mentioned above.

Relating to the present invention, Patent Documents 1 to 3 disclose tetrazoyloxime derivatives having a structure similar to that of the compounds of the present invention.

[Patent Document 1]

Japanese Unexamined Patent Application, First Publication No. 2004-131416

[Patent Document 2]

Japanese Unexamined Patent Application, First Publication No. 2004-131392

[Patent Document 3]

Japanese Unexamined Patent Application, First Publication No. 2003-137875

DISCLOSURE OF THE INVENTION Problems to be Solved by the Invention

However, even the compounds described in these patent documents do not have necessarily a sufficient control effect.

Under these circumstances of prior arts, the present invention has been made and an object thereof is to provide a tetrazoyloxime derivative or a salt thereof, which is excellent in a control effect against plant disease injury, and a plant disease controlling agent containing at least one kind of them as an active ingredient.

Means for Solving the Problems

The present inventors have synthesized a large number of tetrazoyloxime derivatives and intensively studied about bioactivity thereof so as to achieve the above object, and found that the tetrazoyloxime derivative represented by formula (1) shown below and a salt thereof exhibit an excellent control effect against plant disease injury, and are applicable safely without causing phytotoxicity against useful plants. Thus, the present invention has been completed.

According to a first aspect of the present invention, tetrazoyloxime derivatives of [1] to [3] shown below, or salts thereof are provided.

[1] A tetrazoyloxime derivative represented by formula (1):

wherein X represents a halogen atom, a C₁₋₈ alkyl group, a C₁₋₈ alkoxy group, cyano group, a C₁₋₈ alkylsulfonyl group, nitro group, a C₁₋₈ haloalkyl group, or an unsubstituted or substituted aryl group; n1 represents any one of integers of 0 to 5, and when n1 is 2 or more, X(s) may be the same or different with each other; A represents a tetrazoyl group represented by formula (2):

(in which Y represents a C₁₋₈ alkyl group), or a tetrazoyl group represented by formula (3):

(in which Y is the same as defined above); and Het represents a pyridyl group represented by formula (4):

(in which R represents a halogen atom, a cyano group, a nitro group, a hydroxyl group, a thiol group, a formyl group, a carboxyl group, an unsubstituted or substituted amino group, an unsubstituted or substituted C₁₋₈ alkyl group, an unsubstituted or substituted C₂₋₈ alkenyl group, an unsubstituted or substituted C₂₋₈ alkynyl group, an unsubstituted or substituted aryl group, an unsubstituted or substituted heterocyclic group, OR¹, S(O)_(m)R¹, COR¹, or CO₂R¹, R¹ represents an unsubstituted or substituted amino group, an unsubstituted or substituted C₁₋₈ alkyl group, an unsubstituted or substituted C₃₋₈ cycloalkyl group, an unsubstituted or substituted C₂₋₈ alkenyl group, an unsubstituted or substituted C₂₋₈ alkynyl group, or an unsubstituted or substituted aryl group, m represents any one of integers of 0 to 2, n2 represents any one of integers of 0 to 3, and when n2 is 2 or more, plural R(s) may be the same or different from each other, when n2 is 0, Z represents a group represented by formula: Q¹C(═O)NH— (in which Q¹ represents a C₁₋₈ haloalkyl group, a C₂₋₈ haloalkenyl group, a C₂₋₈ alkynyl group, a C₂₋₈ haloalkynyl group, a C₁₋₈ haloalkoxy group, a C₂₋₈ alkenyloxy group, a C₂₋₈ haloalkenyloxy group, a C₂₋₈ alkynyloxy group, a C₂₋₈ haloalkynyloxy group, a C₁₋₈ alkoxy group substituted with an alkoxycarbonylamino group, a C₁₋₈ alkoxy group substituted with a C₃₋₈ cycloalkyl group, a C₁₋₈ branched alkoxy group substituted with an unsubstituted aryl group, a C₁₋₈ alkoxy group substituted with substituted aryl, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted heterocyclic group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted C₁₋₈ alkoxy group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted aryloxy group, an C₁₋₈ alkoxy group substituted with an unsubstituted or substituted aralkyloxy group, a C₂₋₈ alkynyloxy group substituted with an unsubstituted or substituted aryl group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted C₁₋₈ alkylthio group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted arylthio group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted C₁₋₈ alkylsulfinyl group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted arylsulfinyl group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted C₁₋₈ alkylsulfonyl group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted arylsulfonyl group, a C₁₋₈ alkoxy group substituted with an amino group which is unsubstituted or substituted with an (unsubstituted or substituted alkyl group), a C₁₋₈ alkoxy group which is substituted with an amino group substituted with an (unsubstituted or substituted aralkyl group), an unsubstituted or substituted aryloxy group, a C₁₋₈ alkyl group substituted with a carboxyl group, a C₁₋₈ alkyl group substituted with an amino group which is unsubstituted or substituted with an (unsubstituted or substituted aralkyl group), a C₁₋₈ alkyl group substituted with an amino group which is substituted with an (unsubstituted or substituted alkyl group), a C₁₋₈ alkyl group substituted with an unsubstituted or substituted aryloxy group, a C₁₋₈ alkyl group substituted with an acyl group, or a C₁₋₈ alkyl group substituted with an unsubstituted or substituted heterocyclicoxy group), when n2 is 1 and R is a halogen atom, Z represents a hydrogen atom, an amino group, or a group represented by formula: Q²C(═O)NH— (in which Q² represents a hydrogen atom, a C₁₋₈ haloalkyl group, a C₂₋₈ alkenyl group, a C₂₋₈ haloalkenyl group, a C₂₋₈ alkynyl group, a C₂₋₈ haloalkynyl group, a C₁₋₈ alkoxy group, a C₁₋₈ haloalkoxy group, a C₂₋₈ alkenyloxy group, a C₂₋₈ haloalkenyloxy group, a C₂₋₈ alkynyloxy group, a C₂₋₈ haloalkynyloxy group, a C₃₋₈ cycloalkyl group, a C₃₋₈ cycloalkyloxy group, a C₁₋₈ alkylamino group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted amino group, a C₁₋₈ alkoxy group substituted with a C₃₋₈ cycloalkyl group, an unsubstituted or substituted aralkyloxy group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted heterocyclic group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted C₁₋₈ alkoxy group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted aryloxy group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted aralkyloxy group, a C₂₋₈ alkynyloxy group substituted with an unsubstituted or substituted aryl group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted C₁₋₈ alkylthio group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted arylthio group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted C₁₋₈ alkylsulfinyl group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted arylsulfinyl group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted C₁₋₈ alkylsulfonyl group, C₁₋₈ alkoxy group substituted with an unsubstituted or substituted arylsulfonyl group, an unsubstituted or substituted aryloxy group, a C₁₋₈ alkyl group substituted with a carboxyl group, a C₁₋₈ alkyl group substituted with an unsubstituted or substituted amino group, a C₁₋₈ alkyl group substituted with an unsubstituted or substituted aryloxy group, a C₁₋₈ alkyl group substituted with an unsubstituted or substituted C₁₋₈ alkylthio group, a C₁₋₈ alkyl group substituted with an unsubstituted or substituted alkoxy group, a C₁₋₈ alkyl group substituted with an acyl group, or a alkyl group substituted with an unsubstituted or substituted heterocyclicoxy group), when n2 is 1 or more and at least one R is a cyano group, a nitro group, a hydroxyl group, a thiol group, a formyl group, a carboxyl group, an unsubstituted or substituted amino group, an unsubstituted or substituted C₁₋₈ alkyl group, an unsubstituted or substituted C₂₋₈ alkenyl group, an unsubstituted or substituted C₂₋₈ alkynyl group, an unsubstituted or substituted aryl group, an unsubstituted or substituted heterocyclic group, OR¹, S(O)_(m)R¹, COR¹, or CO₂R¹, or when n2 is 2 or more and at least two R(s) are halogen atoms, Z represents a hydrogen atom, an amino group, or a group represented by formula: Q³C(═O)NH— (in which Q³ represents a hydrogen atom, a C₁₋₈ alkyl group, a C₁₋₈ haloalkyl group, a C₂₋₈ alkenyl group, a C₂₋₈ haloalkenyl group, a C₂₋₈ alkynyl group, a C₂₋₈ haloalkynyl group, a C₁₋₈ alkoxy group, a C₁₋₈ haloalkoxy group, a C₂₋₈ alkenyloxy group, a C₂₋₈ haloalkenyloxy group, a C₂₋₈ alkynyloxy group, a C₂₋₈ haloalkynyloxy group, a C₃₋₈ cycloalkyl group, a C₃₋₈ cycloalkyloxy group, a C₁₋₈ alkylamino group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted amino group, a C₁₋₈ alkoxy group substituted with a C₃₋₈ cycloalkyl group, an unsubstituted or substituted aralkyloxy group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted heterocyclic group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted C₁₋₈ alkoxy group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted aryloxy group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted aralkyloxy group, a C₂₋₈ alkynyloxy group substituted with an unsubstituted or substituted aryl group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted C₁₋₈ alkylthio group, a C₁₋₈ alkoxy group substituted with a substituted or unsubstituted arylthio group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted C₁₋₈ alkylsulfinyl group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted arylsulfinyl group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted C₁₋₈ alkylsulfonyl group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted arylsulfonyl group, an unsubstituted or substituted aryloxy group, a C₁₋₈ alkyl group substituted with a carboxyl group, a C₁₋₈ alkyl group substituted with an unsubstituted or substituted amino group, a C₁₋₈ alkyl group substituted with an unsubstituted or substituted aryloxy group, a C₁₋₈ alkyl group substituted with an unsubstituted or substituted C₁₋₈ alkylthio group, a C₁₋₈ alkyl group substituted with an unsubstituted or substituted alkoxy group, an alkyl group substituted with an acyl group, or a C₁₋₈ alkyl group substituted with an unsubstituted or substituted heterocyclicoxy group), or a thiazoyl group represented by formula (5):

(in which R¹¹ represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, a hydroxyl group, a thiol group, a formyl group, a carboxyl group, an unsubstituted or substituted amino group, an unsubstituted or substituted C₁₋₈ alkyl group, an unsubstituted or substituted C₂₋₈ alkenyl group, an unsubstituted or substituted C₂₋₈ alkynyl group, an unsubstituted or substituted aryl group, an unsubstituted or substituted heterocyclic group, OR¹, S(O)_(m)R¹, COR¹, or CO₂R¹, R¹ is the same as defined above, when R¹¹ is a hydrogen atom, Z¹¹ represents a group represented by formula: Q¹C(═O)NH— (in which Q¹ is the same as defined above), when R¹¹ is a halogen atom, Z¹¹ represents a hydrogen atom, an amino group, or a group represented by formula: Q²C(═O)NH— (in which Q² is the same as defined above), and when R¹¹ is a cyano group, a nitro group, a hydroxyl group, a thiol group, a formyl group, a carboxyl group, an unsubstituted or substituted amino group, an unsubstituted or substituted C₁₋₈ alkyl group, an unsubstituted or substituted C₂₋₈ alkenyl group, an unsubstituted or substituted C₂₋₈ alkynyl group, an unsubstituted or substituted aryl group, an unsubstituted or substituted heterocyclic group, OR¹, S(O)_(m)R¹, COR¹, or CO₂R¹, Z¹¹ represents a hydrogen atom, an amino group, or a group represented by formula: Q³C(═O)NH— (in which Q³ is the same as defined above), and a salt thereof. [2] The tetrazoyloxime derivative according to [1], wherein n1 is 0, or X is halogen atom, and a salt thereof. [3] The tetrazoyloxime derivative according to [1] or [2], wherein Y is a methyl group, and a salt thereof.

According to a second aspect of the present invention, a plant disease controlling agent including the tetrazoyloxime derivative according to any one of [1] to [3] or a salt thereof as an active ingredient is provided.

EFFECTS OF THE INVENTION

According to the present invention, a tetrazoyloxime derivative which is excellent in a control effect against plant disease injury, or a salt thereof, and a plant disease controlling agent containing the same as an active ingredient are provided.

BEST MODE FOR CARRYING OUT THE INVENTION

The present invention will be explained in detail by itemizing into 1) a tetrazoyloxime derivative and a salt thereof, and 2) a plant disease controlling agent.

1) Tetrazoyloxime Derivative and a Salt Thereof.

The first aspect of the present invention is directed to a tetrazoyloxime derivative represented by formula (1) shown above, and a salt thereof.

In formula (1) shown above, X represents a halogen atom, a C₁₋₈ alkyl group, a C₁₋₈ alkoxy group, a cyano group, a C₁₋₈ alkylsulfonyl group, a nitro group, a C₁₋₈ haloalkyl group, or an unsubstituted or substituted aryl group.

Specific examples of the halogen atom for X include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

Specific examples of the C₁₋₈ alkyl group include a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an i-butyl group, an s-butyl group, a t-butyl group, an n-pentyl group, and an n-hexyl group.

Specific examples of the C₁₋₈ alkoxy group include a methoxy group, an ethoxy group, an n-propoxy group, an i-propoxy group, an n-butoxy group, an i-butoxy group, an s-butoxy group, a t-butoxy group, and an n-hexyloxy group.

Specific examples of the C₁₋₈ alkylsulfonyl group include a methylsulfonyl group, an ethylsulfonyl group, an n-propylsulfonyl group, an isopropylsulfonyl group, and a t-butylsulfonyl group.

Specific examples of the C₁₋₈ haloalkyl group include a fluoromethyl group, a chloromethyl group, a bromomethyl group, a difluoromethyl group, a dichloromethyl group, a trifluoromethyl group, a trichloromethyl group, a trifluoroethyl group, a pentafluoroethyl group, a 3,3,3,2,2-pentafluoropropyl group, and a 2,2,2-trifluoro-1-trifluoromethylethyl group.

An aryl group an unsubstituted or substituted aryl group means a monocyclic or polycyclic aryl group, and the polycyclic aryl group includes, in addition to a completely unsaturated group, a partially unsaturated group.

Specifically, a phenyl group, a 1-naphthyl group, a 2-naphthyl group, an azulenyl group, an indanyl group, and a tetralinyl group are exemplified, and a C₆₋₁₀ aryl group is preferred.

The substituent of the aryl group of the unsubstituted or substituted aryl group is not particularly limited as long as it is chemically acceptable. Specific examples of the substituent include substituents shown below:

(1) halogen atoms such as a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, (2) alkyl groups such as a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an s-butyl group, an i-butyl group, a t-butyl group, an n-pentyl group, and an n-hexyl group, (3) cycloalkyl groups such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group, (4) alkoxy groups such as a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, an i-butoxy group, an s-butoxy group, and a t-butoxy group, (5) alkenyl groups such as a vinyl group, a 1-propenyl group, a 2-propenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-methyl-2-propenyl group, a 2-methyl-2-propenyl group, a 1-pentenyl group, a 2-pentenyl group, a 3-pentenyl group, a 4-pentenyl group, a 1-methyl-2-butenyl group, a 2-methyl-2-butenyl group, a 1-hexenyl group, a 2-hexenyl group, a 3-hexenyl group, a 4-hexenyl group, and a 5-hexenyl group, (6) cycloalkenyl groups such as a 2-cyclopropenyl group, a 2-cyclopentenyl group, a 3-cyclohexenyl group, and a 4-cyclooctenyl group, (7) alkenyloxy groups such as a vinyloxy group, an allyloxy group, a 1-propenyloxy group, a 2-butenyloxy group, a (8) alkynyl groups such as ethynyl group, a 1-propynyl group, a 2-propynyl group, a 1-butynyl group, a 2-butynyl group, a 3-butynyl group, a 1-methyl-2-propynyl group, a 2-methyl-3-butynyl group, a 1-pentynyl group, a 2-pentynyl group, a 3-pentynyl group, a 4-pentynyl group, a 1-methyl-2-butynyl group, a 2-methyl-3-pentynyl group, a 1-hexynyl group, and a 1,1-dimethyl-2-butynyl group, (9) alkynyloxy groups such as an ethynyloxy group and a propargyloxy group, (10) aryl groups such as a phenyl group, a 1-naphthyl group, and a 2-naphthyl group, (11) aryloxy groups such as a phenoxy group and a 1-naphthoxy group, (12) aralkyl groups such as a benzyl group and a phenethyl group, (13) aralkyloxy groups such as a benzyloxy group and a phenethyloxy group, (14) acyl groups such as a formyl group, an acetyl group, a propionyl group, a benzoyl group, a cyclohexylcarbonyl group, and a phthaloyl group, (15) alkoxycarbonyl groups such as a methoxycarbonyl group, an ethoxycarbonyl group, an n-propoxycarbonyl group, an isopropoxycarbonyl group, an n-butoxycarbonyl group, and a t-butoxycarbonyl group, (16) carboxyl groups, (17) hydroxyl groups, (18) haloalkyl groups such as a chloromethyl group, a chloroethyl group, a 1,2-dichloro-n-propyl group, a 1-fluoro-n-butyl group, a perfluoro-n-pentyl group, a haloalkoxy groups such as 2-chloro-n-propoxy group, a 2,3-dichlorobutoxy group, and a trifluoromethoxy group, (19) haloalkenyl groups such as a 2-chloro-1-propenyl group and a 2-fluoro-1-butenyl group, (20) haloalkynyl groups such as a 4,4-dichloro-1-butynyl group, a 4-fluoro-1-pentynyl group, and a 5-bromo-2-pentynyl group, (21) haloalkenyloxy groups such as a 2-chloro-1-propenyloxy group and a 3-bromo-2-butenyloxy group, (22) haloalkynyl groups such as a 3-chloro-propargyl group and a 3-iodo-propargyl group, (23) haloalkynyloxy groups such as a 3-chloro-propargyloxy group and a 3-iodo-propargyloxy group, (24) haloaryl groups such as a 4-chlorophenyl group, a 4-fluorophenyl group, and a 2,4-dichlorophenyl group, (25) haloaryloxy groups such as a 4-fluorophenoxy group and a 4-chloro-1-naphthoxy group, (26) halogen-substituted acyl groups such as a chloroacetyl group, a trifluoroacetyl group, a trichloroacetyl group, and a 4-chlorobenzoyl group, (27) alkoxyalkyl groups such as a methoxymethyl group, an ethoxymethyl group, a 1-ethoxyethyl group, and a 2-ethoxyethyl group, (28) alkoxyalkoxy groups such as a methoxymethoxy group, an ethoxymethoxy group, a 1-ethoxyethoxy group, and a 2-ethoxyethoxy group, (29) cyano groups, (30) isocyano groups, (31) nitro groups, (32) isocyanato groups, (33) cyanato groups, (34) amino groups, (35) alkylamino groups such as a methylamino group, a dimethylamino group, and a diethylamino group, (36) arylamino groups such as an anilino group, a naphthylamino group, and an anthranyl amino group, (37) aralkylamino groups such as a benzylamino group and a phenethylamino group, (38) alkylsulfonylamino groups such as a methylsulfonylamino group, an ethylsulfonylamino group, an n-propylsulfonylamino group, an isopropylsulfonylamino group, and an n-butylsulfonylamino group, (39) arylsulfonylamino groups such as a phenylsulfonylamino group, (40) heteroarylsulfonylamino groups such as a piperazinylsulfonylamino group (41) acylamino groups such as a formylamino group, an acetylamino group, a propanoylamino group, a butyrylamino group, an isopropylcarbonylamino group, and a benzoylamino group (42) alkoxycarbonylamino groups such as a methoxycarbonylamino group and an ethoxycarbonylamino group, (43) haloalkylsulfonylamino groups such as a fluoromethylsulfonylamino group, a chloromethylsulfonylamino group, a bromomethylsulfonylamino group, a difluoromethylsulfonylamino group, a dichloromethylsulfonylamino group, a 1,1-difluoroethylsulfonylamino group, a trifluoromethylsulfonylamino group, a 2,2,2-trifluoroethylsulfonylamino group, and a pentafluorosulfonylamino group, (44) bis(alkylsulfonyl)amino groups such as a bis(methylsulfonyl)amino group, a bis(ethylsulfonyl)amino group, an (ethylsulfonyl)(methylsulfonyl)amino group, a bis(n-propylsulfonyl)amino group, a bis(isopropylsulfonyl)amino group, a bis(n-butylsulfonyl)amino group, and a bis(t-butylsulfonyl)amino group, (45) bis(haloalkylsulfonyl)amino groups such as a bis(fluoromethylsulfonyl)amino group, a bis(chloromethylsulfonyl)amino group, a bis(bromomethylsulfonyl)amino group, a bis(dichloromethylsulfonyl)amino group, a bis(1,1-difluoroethylsulfonyl)amino group, a bis(trifluoromethylsulfonyl)amino group, a bis(2,2,2-trifluoroethyl)amino group, and a bis(pentafluoroethylsulfonyl)amino group, (46) unsubstituted or substituted hydrazino groups such as a hydrazino group, an N′-phenylhydrazino group, an N′-methoxycarbonylhydrazino group, an N′-acetylhydrazino group, and an N′-methylhydrazino group, (47) unsubstituted or substituted aminocarbonyl groups such as an aminocarbonyl group, a dimethylaminocarbonyl group, a phenylaminocarbonyl group, and an N-phenyl-N-methylcarbonyl group, (48) unsubstituted or substituted hydrazinocarbonyl groups such as a hydrazinocarbonyl group, an N′-methylhydrazinocarbonyl group, and an N′-phenylhydrazinocarbonyl group, (49) unsubstituted or substituted iminoalkyl groups such as an N-methyliminomethyl group, a 1-N-phenyliminoethyl group, an N-hydroxyiminomethyl group, and an N-methoxyiminomethyl group, (50) thiol groups, (51) isothiocyanato groups, (52) thiocyanato groups, (53) alkylthio groups such as a methylthio group, an ethylthio group, an n-propylthio group, an isopropylthio group, an n-butylthio group, an isobutylthio group, an s-butylthio group, and a t-butylthio group, (54) alkenylthio groups such as vinylthio group, an allylthio group, (55) alkynylthio groups such as an ethynylthio group and a propargylthio group, (56) arylthio groups such as a phenylthio group and a naphthylthio group, (57) heteroarylthio groups such as 2-piperidylthio group, a 3-pyridazylthio group, (58) aralkylthio groups such as a benzylthio group and a phenethylthio group, (59) heteroarylalkylthio groups such as a 2-pyridylmethylthio group and a 2-furylmethylthio group, (60) alkylthiocarbonyl groups such as a methylthiocarbonyl group, an ethylthiocarbonyl group, an n-propylthiocarbonyl group, an isopropylthiocarbonyl group, an n-butylthiocarbonyl group, an isobutylthiocarbonyl group, an s-butylthiocarbonyl group, and a t-butylthiocarbonyl group, (61) alkylthioalkyl groups such as a methylthiomethyl group and a 1-methylthioethyl group, (62) arylthioalkyl groups such as a phenylthiomethyl group and a 1-phenylthioethyl group, (63) alkylthioalkoxy groups such as a methylthiomethoxy group and a 1-methylthioethoxy group, (64) arylthioalkoxy groups such as a phenylthiomethoxy group and a 1-phenylthioethoxy group, (65) alkylsulfinyl groups such as a methylsulfinyl group, an ethylsulfinyl group, and a t-butylsulfenyl group, (66) alkenylsulfinyl groups such as an allylsulfinyl group, (67) alkynylsulfinyl groups such as a propargylsulfinyl group, (68) arylsulfinyl groups such as a phenylsulfinyl group, (69) heteroarylsulfinyl groups such as a 2-pyridylsulfinyl group and a 3-pyridylsulfinyl group, (70) aralkylsulfinyl groups such as a benzylsulfinyl group and a phenethylsulfinyl group, (71) heteroarylalkylsulfenyl groups such as a 2-pyridylmethylsulfinyl group and a 3-pyridylmethylsulfinyl group, (72) alkylsulfonyl groups such as a methylsulfonyl group, an ethylsulfonyl group, and a t-butylsulfonyl group, (73) alkenylsulfonyl groups such as an allylsulfonyl group, (74) alkynylsulfonyl groups such as a propargylsulfonyl group, (75) arylsulfonyl groups such as a phenylsulfonyl group, (76) heteroarylsulfonyl groups such as 2-pyridylsulfonyl group and a 3-pyridylsulfonyl group, (77) aralkylsulfonyl groups such as a benzylsulfonyl group and a phenethylsulfonyl group, (78) heteroarylalkylsulfonyl groups such as a 2-pyridylmethylsulfonyl group and a 3-pyridylmethylsulfonyl group, (79) unsaturated 5-membered heterocyclic groups such as a furan-2-yl group, a furan-3-yl group, a thiophen-2-yl group, a thiophen-3-yl group, a pyrrol-2-yl group, a pyrrol-3-yl group, an oxazol-2-yl group, an oxazol-4-yl group, an oxazol-5-yl group, a thiazol-2-yl group, a thiazol-4-yl group, a thiazol-5-yl group, an isooxazol-3-yl group, an isooxazol-4-yl group, an isooxazol-5-yl group, an isothiazol-3-yl group, an isothiazol-4-yl group, an isothiazol-5-yl group, an imidazol-2-yl group, an imidazol-4-yl group, an imidazol-5-yl group, a pyrazol-3-yl group, a pyrazol-4-yl group, a pyrazol-5-yl group, a 1,3,4-oxadiazol-2-yl group, a 1,3,4-thiadiazol-2-yl group, a 1,2,3-triazol-4-yl group, a 1,2,4-triazol-3-yl group, and a 1,2,4-triazol-5-yl group, (80) unsaturated 6-membered heterocyclic groups such as a pyridin-2-yl group, a pyridin-3-yl group, a pyridin-4-yl group, a 5-chloro-3-pyridyl group, a 3-trifluoromethyl-2-pyridyl group, a pyridazin-3-yl group, a pyridazin-4-yl group, a pyrazin-2-yl group, a pyrimidin-5-yl group, a 1,3,5-triazin-2-yl group, and a 1,2,4-triazin-3-yl group, (81) saturated or partially unsaturated heterocyclic groups such as a tetrahydrofuran-2-yl group, a tetrahydropyran-4-yl group, a piperidin-3-yl group, a pyrrolidin-2-yl group, a morpholino group, a piperidino group, an N-methylpiperazino group, and an oxazolin-2-yl group, (82) heterocyclicoxy groups such as a 2-pyridyloxy group and a 3-isoxazolyloxy group, (83) heteroarylalkyl groups such as a 2-pyridylmethyl group and a 3-pyridylmethyl group, and (84) heteroarylalkoxy groups such as a 2-pyridylmethoxy group and a 3-pyridylmethoxy group.

These substituents exemplified in (1) to (84) can also be substituted with those exemplified in (1) to (84).

Specific examples of the substituted aryl group include a 4-fluorophenyl group, a 2,4-dichlorophenyl group, a 3,5-dichlorophenyl group, a 2,6-difluorophenyl group, a 4-methoxyphenyl group, and a 3,4-dimethoxyphenyl group.

Among these, X is preferably a halogen atom.

n1 represents any one of integers of 0 to 5, and preferably any one of integers of 0 to 3.

When n1 is 2 or more, X(s) may be the same or different with each other.

A represents a tetrazoyl group represented by formula (2) or formula (3), and preferably formula (2).

In formulas (2) and (3), Y represents a C₁₋₈ alkyl group. Examples of the C₁₋₈ alkyl group include a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an i-butyl group, an s-butyl group, a t-butyl group, an n-pentyl group, and an n-hexyl group.

Among these, Y is preferably a C₁₋₃ alkyl group, and particularly preferably a methyl group.

Het represents a pyridyl group represented by formula (4) or a thiazolyl group represented by formula (5).

In formulas (4) and (5), R represents a halogen atom, a cyano group, a nitro group, a hydroxyl group, a thiol group, a formyl group, a carboxyl group, an unsubstituted or substituted amino group, an unsubstituted or substituted C₁₋₈ alkyl group, an unsubstituted or substituted C₂₋₈ alkenyl group, an unsubstituted or substituted C₂₋₈ alkynyl group, an unsubstituted or substituted aryl group, an unsubstituted or substituted heterocyclic group, OR¹, S(O)_(m)R¹, COR¹, or CO₂R¹.

Specific examples of the halogen atom, the C₁₋₈ alkyl group of the unsubstituted or substituted C₁₋₈ alkyl group, and the aryl group of the unsubstituted or substituted aryl group for R are the same as those for X.

Specific examples of the C₂₋₈ alkenyl group of the unsubstituted or substituted C₂₋₈ alkenyl group for R include a vinyl group, a 1-propenyl group, a 2-propenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-methyl-2-propenyl group, a 2-methyl-2-propenyl group, a 1-pentenyl group, a 2-pentenyl group, a 3-pentenyl group, a 4-pentenyl group, a 1-methyl-2-butenyl group, a 2-methyl-2-butenyl group, a 1-hexenyl group, a 2-hexenyl group, a 3-hexenyl group, a 4-hexenyl group, and a 5-hexenyl group.

Specific examples of the C₂₋₈ alkynyl group of the unsubstituted or substituted C₂₋₈ alkynyl group for R include an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 1-butynyl group, a 2-butynyl group, a 3-butynyl group, a 1-methyl-2-propynyl group, a 2-methyl-3-butynyl group, a 1-pentynyl group, a 2-pentynyl group, a 3-pentynyl group, a 4-pentynyl group, a 1-methyl-2-butynyl group, a 2-methyl-3-pentynyl group, a 1-hexynyl group, and a 1,1-dimethyl-2-butynyl group.

Specific examples of the heterocyclic group of the unsubstituted or substituted heterocyclic group for R include unsaturated 5-membered heterocyclic groups such as a furan-2-yl group, a furan-3-yl group, a thiophen-2-yl group, a thiophen-3-yl group, a pyrrol-2-yl group, a pyrrol-3-yl group, an oxazol-2-yl group, an oxazol-4-yl group, an oxazol-5-yl group, a thiazol-2-yl group, a thiazol-4-yl group, a thiazol-5-yl group, an isooxazol-3-yl group, an isooxazol-4-yl group, an isooxazol-5-yl group, an isothiazol-3-yl group, an isothiazol-4-yl group, an isothiazol-5-yl group, an imidazol-2-yl group, an imidazol-4-yl group, an imidazol-5-yl group, a pyrazol-3-yl group, a pyrazol-4-yl group, a pyrazol-5-yl group, a 1,3,4-oxadiazol-2-yl group, a 1,3,4-thiadiazol-2-yl group, a 1,2,3-triazol-4-yl group, a 1,2,4-triazol-3-yl group, and a 1,2,4-triazol-5-yl group; unsaturated 6-membered heterocyclic groups such as a pyridin-2-yl group, a pyridin-3-yl group, a pyridin-4-yl group, a 5-chloro-3-pyridyl group, a 3-trifluoromethyl-2-pyridyl group, a pyridazin-3-yl group, a pyridazin-4-yl group, a pyrazin-2-yl group, a pyrimidin-5-yl group, a 1,3,5-triazin-2-yl group, and a 1,2,4-triazin-3-yl group; and saturated or partially unsaturated heterocyclic groups such as a tetrahydrofuran-2-yl group, a tetrahydropyran-4-yl group, a piperidin-3-yl group, a pyrrolidin-2-yl group, a morpholino group, a piperidino group, a piperazino group, an N-methylpiperazino group, an aziridino group, an azetidino group, a pyrrolidino group, a morpholino group, and an oxazolin-2-yl group.

As the substituent of the amino group, the C₁₋₈ alkyl group, the C₂₋₈ alkenyl group, the C₂₋₈ alkynyl group, the aryl group, and the heteroaryl group, for example, the same substituents as those of the aryl group for X can be exemplified in a chemically acceptable range.

Specific examples of the substituted amino group include a methylamino group, a dimethylamino group, a methylethylamino group, a diethylamino group, a t-butoxycarbonylmethylamino group, a t-butoxycarbonylamino group, an acetylmethylamino group, an acetylethylamino group, and a benzoylmethylamino group.

Specific examples of the substituted C₁₋₈ alkyl group include a chloromethyl group, a methoxymethyl group, a methylthiomethyl group, a methylsulfonylmethyl group, a dimethylaminomethyl group, a trichloromethyl group, a trifluoromethyl group, and a 2-chloroethyl group.

Specific examples of the substituted C₂₋₈ alkenyl group include a 2-chloroethenyl group, a 2-fluoroethenyl group, a 3,3,3-trifluoro-1-pentenyl group, a 1,2,2-trifluoroethenyl group, a 2,3,3-trifluoro-2-propenyl group, a 2,3,3-triiodo-2-propenyl group, and a 2-methoxyethenyl group.

Specific examples of the substituted C₂₋₈ alkynyl group include a 2-chloroethynyl group, a 2-fluoroethynyl group, a 3-fluoro-1-propynyl group, a 3,3,3-trifluoro-1-propynyl group, a 3-fluoro-2-propynyl group, and a 3-iodo-2-propynyl group.

Specific examples of the substituted aryl group include a 4-chlorophenyl group, a 2,4-dichlorophenyl group, a 3,4-dichlorophenyl group, a 4-trifluoromethylphenyl group, a 4-methoxyphenyl group, a 3,4-dimethoxyphenyl group, a 3,4-methylenedioxyphenyl group, a 4-trifluoromethoxyphenyl group, and a 4-methoxy-1-naphthyl group.

Specific examples of the substituted heterocyclic group include a 3-trifluoromethylpyridin-2-yl group, a 4-trifluoromethoxy-2-pyridyl group, a 3-methyl-1-pyrazolyl group, a 4-trifluoromethyl-1-imidazolyl group, and a 3,4-difluoropyrrolidino group.

R¹ of OR¹, COR¹, S(O)_(m)R¹, and CO₂R¹ for R represents an unsubstituted or substituted amino group, an unsubstituted or substituted C₁₋₈ alkyl group, an unsubstituted or substituted C₃₋₈ cycloalkyl group, an unsubstituted or substituted C₂₋₈ alkenyl group, an unsubstituted or substituted C₂₋₈ alkynyl group, an unsubstituted or substituted aryl group, or an unsubstituted or substituted heterocyclic group.

As specific examples of the unsubstituted or substituted amino group, the unsubstituted or substituted C₁₋₈ alkyl group, the unsubstituted or substituted C₂₋₈ alkenyl group, the unsubstituted or substituted C₂₋₈ alkynyl group, the unsubstituted or substituted aryl group, and the unsubstituted or substituted heterocyclic group, for example, the same groups as those for R can be exemplified.

Specific examples of the C₃₋₈ cycloalkyl group of the unsubstituted or substituted C₃₋₈ cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group.

Specific examples of the substituted C₃₋₈ cycloalkyl group include a 2-methylcyclopropyl group, a 2-chloro-cyclopropyl group, a 2-trifluoromethylcyclobutyl group, a 2,3,4-trifluorocyclopentyl group, and a 2,2,3,3-tetrafluorocyclopropyl group.

Specific examples of OR¹ include a methoxy group, an ethoxy group, an n-propoxy group, an i-propoxy group, an n-butoxy group, an s-butoxy group, an i-butoxy group, a t-butoxy group, a methoxymethoxy group, an ethoxymethoxy group, a 2-methoxyethoxy group, a 1-ethoxyethoxy group, a vinyloxy group, a 1-propenyloxy group, a 2-propenyloxy group, an ethynyloxy group, a 1-propynyloxy group, a 2-propynyloxy group, an aminooxy group, a methylaminooxy group, a diethylaminooxy group, a methoxycarbonylaminooxy group, a phenoxy group, a trichloromethoxy group, a trifluoromethoxy group, a difluoromethoxy group, a 2,2,2-trifluoroethoxy group, a pentafluoroethoxy group, and a 2-fluoroethoxy group.

Specific examples of COR¹ include an acetyl group, a benzoyl group, a propanoyl group, an i-propylcarbonyl group, a t-butylcarbonyl group, a cyclopropylcarbonyl group, a cyclobutylcarbonyl group, a cyclopentylcarbonyl group, a vinylcarbonyl group, a 1-propenylcarbonyl group, a 2-propenylcarbonyl group, an i-propenylcarbonyl group, a 1-propynylcarbonyl group, a 2-propynylcarbonyl group, a 3-butenylcarbonyl group, a methylaminocarbonyl group, a dimethylaminocarbonyl group, an N-methyl-N-ethylaminocarbonyl group, an aziridinocarbonyl group, an azetidinocarbonyl group, a pyrrolidinocarbonyl group, a piperidinocarbonyl group, a morpholinocarbonyl group, a piperazinocarbonyl group, and an N-methylpiperazinocarbonyl group.

Specific examples of CO₂R¹ include a methoxycarbonyl group, a trifluoromethoxycarbonyl group, a 1-pentenyloxycarbonyl group, a 2-propynyloxycarbonyl group, and a phenoxycarbonyl group.

Specific examples of S(O)_(m)R¹ for R include a dimethylaminothio group, a chloromethylthio group, a 3-butenylthio group, an ethynylthio group, a 3-methylphenylthio group, a methylsulfinyl group, an ethylsulfinyl group, a 1-butenylsulfinyl group, an n-hexylsulfinyl group, a 2,3-dimethylphenylsulfinyl group, a methylsulfonyl group, a dimethylaminosulfonyl group, an N-ethyl-N-methylaminosulfonyl group, an n-hexylsulfonyl group, a 2-methyl-2-butenylsulfonyl group, a 2-propynylsulfonyl group, a 2-naphthylsulfonyl group, a phenylsulfonyl group, a 2-nitrophenylsulfonyl group, and a p-tolylsulfonyl group.

Among these, a halogen atom, an unsubstituted or substituted amino group, a C₁₋₈ alkyl group, OR₁, and SR₁ are preferable, and an unsubstituted or substituted amino group, a C₁₋₈ alkyl group, OR₁, and SR₁ are more preferable.

An amino group and a dialkylamino group can be preferably exemplified as the unsubstituted or substituted amino group, a C₁₋₄ alkyl group can be preferably exemplified as the C₁₋₈ alkyl group, a C₁₋₄ alkoxy group can be preferably exemplified as OR₁, and a C₁₋₄ alkylthio group can be preferably exemplified as SR₁.

m represents any one of integers of 0 to 2.

n2 represents any one of integers of 0 to 3. When n2 is 2 or more, plural R(s) may be the same or different from each other.

When n2 is 0, Z represents a group represented by formula: Q¹C(═O)NH— (in which Q¹ represents a C₁₋₈ haloalkyl group, a C₂₋₈ haloalkenyl group, a C₂₋₈ alkynyl group, a C₂₋₈ haloalkynyl group, a C₁₋₈ haloalkoxy group, a C₂₋₈ alkenyloxy group, a C₂₋₈ haloalkenyloxy group, a C₂₋₈ alkynyloxy group, a C₂₋₈ haloalkynyloxy group, a C₁₋₈ alkoxy group substituted with an alkoxycarbonylamino group, a C₁₋₈ alkoxy group substituted with a C₃₋₈ cycloalkyl group, a C₁₋₈ branched alkoxy group substituted with an unsubstituted aryl group, a C₁₋₈ alkoxy group substituted with a substituted aryl group, a C₁₋₈ alkoxy group substituted with a substituted or unsubstituted heterocyclic group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted C₁₋₈ alkoxy group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted aryloxy group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted aralkyloxy group, a C₂₋₈ alkynyloxy group substituted with an unsubstituted or substituted aryl group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted C₁₋₈ alkylthio group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted arylthio group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted C₁₋₈ alkylsulfinyl group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted arylsulfinyl group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted C₁₋₈ alkylsulfonyl group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted arylsulfonyl group, a C₁₋₈ alkoxy group substituted with an amino group which is unsubstituted or substituted with an (unsubstituted or substituted alkyl group), a C₁₋₈ alkoxy group which is substituted with an amino group substituted with an (unsubstituted or substituted aralkyl group), an unsubstituted or substituted aryloxy group, a C₁₋₈ alkyl group substituted with a carboxyl group, a C₁₋₈ alkyl group substituted with an amino group which is unsubstituted or substituted with an (unsubstituted or substituted aralkyl group), a C₁₋₈ alkyl group substituted with an amino group which is substituted with an (unsubstituted or substituted alkyl group), a C₁₋₈ alkyl group substituted with an unsubstituted or substituted aryloxy group, a C₁₋₈ alkyl group substituted with an acyl group, or a C₁₋₈ alkyl group substituted with an unsubstituted or substituted heterocyclic group).

Specific examples of the C₁₋₈ haloalkyl group for Q¹ include a chloromethyl group, a chloroethyl group, a 1,2-dichloro-n-propyl group, a 1-fluoro-n-butyl group, and a perfluoro-n-pentyl group.

Specific examples of the C₂₋₈ haloalkenyl group for Q¹ include a 1-chlorovinyl group, a 2-bromovinyl group, a 3-fluoroallyl group, and a 2-fluorocrotyl group.

Specific examples of the C₂₋₈ alkynyl group for Q¹ include an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 1-butynyl group, a 2-butynyl group, a 3-butynyl group, a 1-methyl-2-propynyl group, a 2-methyl-3-butynyl group, a 1-pentynyl group, a 2-pentynyl group, a 3-pentynyl group, a 4-pentynyl group, a 1-methyl-2-butynyl group, a 2-methyl-3-pentynyl group, a 1-hexynyl group, and a 1,1-dimethyl-2-butynyl group.

Specific examples of the C₂₋₈ haloalkynyl group for Q¹ include a chloroethynyl group, a bromoethynyl group, an iodoethynyl group, a 3-chloro-1-propynyl group, a 3-chloro-1-butynyl group, and a 3-bromo-1-butynyl group.

Specific examples of the C₁₋₈ haloalkoxy group for Q¹ include a chloromethoxy group, a difluoromethoxy group, a trifluoromethoxy group, a 1,1-difluoroethoxy group, and a hexafluoroethoxy group.

Specific examples of the C₂₋₈ alkenyloxy group for Q¹ include an ethenyloxy group, a 1-propenyloxy group, a 1-methylvinyloxy group, an allyloxy group, a 1-methylallyloxy group, and a 2-butenyloxy group.

Specific examples of the C₂₋₈ haloalkenyloxy group for Q¹ include a 3-chloro-2-propenyloxy group, a 3,3-dichloro-2-propenyloxy group, a 4-chloro-2-butenyloxy group, a 4,4-dichloro-3-butenyloxy group, and a 4,4-difluoro-3-butenyloxy group.

Specific examples of the C₂₋₈ alkynyloxy group for Q¹ include a 2-propynyloxy group, a 2-butynyloxy group, and a 1-methyl-2-propynyloxy group.

Specific examples of the C₂₋₈ haloalkynyloxy group for Q¹ include a 2-chloroethynyloxy group, a 3-chloro-2-propynyloxy group, and a 3-fluoro-2-propynyloxy group.

Specific examples of the alkoxycarbonyl group of the C₁₋₈ alkoxy group substituted with an alkoxycarbonylamino group for Q¹ include a methoxycarbonyl group, an ethoxycarbonyl group, an n-propoxycarbonyl group, an isopropoxycarbonyl group, an n-butoxycarbonyl group, and a t-butoxycarbonyl group. As the C₁₋₈ alkoxy group, for example, the same alkoxy groups as those for X can be exemplified. Hereinafter, specific examples of the C₁₋₈ alkoxy group are the same specific examples. Specific examples of the C₁₋₈ alkoxy group substituted with an alkoxycarbonylamino group include an N-methoxycarbonylaminomethoxy group, an N-t-butoxycarbonylaminomethoxy group, a 2-(N-ethoxycarbonylamino)ethoxy group, and a 2-(N-t-butoxycarbonyl-N-benzylamino)ethoxy group.

Specific examples of the C₃₋₈ cycloalkyl group of the C₁₋₈ alkoxy group substituted with a C₃₋₈ cycloalkyl group for Q¹ include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group. Specific examples of the C₁₋₈ alkoxy group substituted with a C₃₋₈ cycloalkyl group include a cyclopropylmethoxy group, a 1-cyclopropyl-ethoxy group, a cyclohexylmethoxy group, and a 2-cyclohexyl-ethoxy group.

Specific examples of the C₁₋₈ branched alkoxy group substituted with an unsubstituted aryl group include a 1-phenylethoxy group, a 1-phenyl-1-methylethoxy group, and a 2-phenyl-1-methylethoxy group.

As the aryl group of the C₁₋₈ alkoxy group substituted with a substituted aryl group for Q¹, for example, the same aryl groups as those for X can be exemplified. The substituent of the aryl group is not particularly limited and, for example, the same substituents as those of the aryl group for X can be exemplified in a chemically acceptable range. Specific examples of the C₁₋₈ alkoxy group substituted with a substituted aryl group include a 2-methylphenylmethoxy group, a 3-methylphenylmethoxy group, a 4-chlorophenylmethoxy group, a 1-(4-chlorophenyl)ethoxy group, a 3-chlorophenylmethoxy group, a 2-methoxyphenylmethoxy group, a 3-methoxyphenylmethoxy group, a 4-methylsulfonylphenylmethoxy group, and a 3-phenylphenylmethoxy group.

As the heterocyclic group of the C₁₋₈ alkoxy group substituted with an unsubstituted or substituted heterocyclic group for Q¹, for example, the same heterocyclic groups as those for R can be exemplified. The substituent of the heterocycle is not particularly limited and, for example, the same substituents as those of the aryl group for X can be exemplified in a chemically acceptable range. Specific examples of the C₁₋₈ alkoxy group substituted with an unsubstituted or substituted heterocyclic group include a 2-pyridylmethoxy group, a 6-methylpyridin-2-ylmethoxy group, a 4-pyridylmethoxy group, a 1-(4-pyridyl)-1-methylethoxy group, a 2-oxazolylmethoxy group, and a 2-benzoxazolylmethoxy group.

The substituent of the C₁₋₈ alkoxy group substituted with an unsubstituted or substituted C₁₋₈ alkoxy group for Q¹ is not particularly limited and, for example, the same substituents as those of the aryl group for X can be exemplified in a chemically acceptable range. Specific examples of the alkoxy group substituted with an unsubstituted or substituted C₁₋₈ alkoxy group include a methoxymethoxy group, an ethoxymethoxy group, a 2-isopropoxyethoxy group, a 2-(methoxyethoxy)ethoxy group, a 2-trifluoromethoxyethoxy group, and a 2-pentafluoroethoxyethoxy group.

Specific examples of the aryloxy group of the C₁₋₈ alkoxy group substituted with an unsubstituted or substituted aryloxy group for Q¹ include a phenoxy group and a 1-naphthoxy group. The substituent of the aryloxy group is not particularly limited and, for example, the same substituents as those of the aryl group for X can be exemplified in a chemically acceptable range. Specific examples of the C₁₋₈ alkoxy group substituted with an unsubstituted or substituted aryloxy group include a phenoxymethoxy group, a 2-phenoxyethoxy group, a 2-(4-chlorophenoxy)ethoxy group, and a 2-(4-methoxyphenoxy)ethoxy group.

As the aralkyloxy group of the C₁₋₈ alkoxy group substituted with an unsubstituted or substituted aralkyloxy group for Q¹, for example, a benzyloxy group and a phenethyloxy group can be exemplified. The substituent thereof is not particularly limited and, for example, the same substituents as those of the aryl group for X can be exemplified in a chemically acceptable range. Specific examples of the C₁₋₈ alkoxy group substituted with an unsubstituted or substituted aralkyloxy group include a benzyloxymethoxy group, a 2-benzyloxyethoxy group, a phenethyloxymethoxy group, and a (4-chlorophenylmethoxy)methoxy group.

As the aryl group of the C₂₋₈ alkynyloxy group substituted with an unsubstituted or substituted aryl group for Q¹, for example, the same aryl groups as those for X can be exemplified. As the C₂₋₈ alkynyloxy group, for example, the same alkynyl groups as those for R can be exemplified. The substituent of the aryl group is not particularly limited and, for example, the same substituents as those of the aryl group for X can be exemplified in a chemically acceptable range. Specific examples of the C₂₋₈ alkynyloxy group substituted with an unsubstituted or substituted aryl group include a 3-phenyl-2-propynyloxy group, a 1-phenyl-2-propynyloxy group, and a 3-phenyl-1,1-dimethyl-2-propynyloxy group.

Specific examples of the alkylthio group of the C₁₋₈ alkoxy group substituted with an unsubstituted or substituted C₁₋₈ alkylthio group for Q¹ include a methylthio group, an ethylthio group, an n-propylthio group, an isopropylthio group, an n-butylthio group, an isobutylthio group, an s-butylthio group, and a t-butylthio group. The substituent thereof is not particularly limited and, for example, the same substituents as those of the aryl group for X can be exemplified in a chemically acceptable range. Specific examples of the C₁₋₈ alkoxy group substituted with an unsubstituted or substituted C₁₋₈ alkylthio group include a methylthiomethoxy group, a methylthio-n-butoxy group, and a 1-methylthioethoxy group.

Specific examples of the arylthio group of the C₁₋₈ alkoxy group substituted with an unsubstituted or substituted arylthio group for Q¹ include a phenylthio group and a naphthylthio group. The substituent thereof is not particularly limited and, for example, the same substituents as those of the aryl group for X can be exemplified in a chemically acceptable range. Specific examples of the C₁₋₈ alkoxy group substituted with a substituted or unsubstituted arylthio group include a phenylthiomethoxy group, a 2-phenylthioethoxy group, a naphthylthiomethoxy group, and a 1-phenylthioethoxy group.

Specific examples of the alkylsulfinyl group of the C₁₋₈ alkoxy group substituted with an unsubstituted or substituted C₁₋₈ alkylsulfinyl group for Q¹ include a methylsulfinyl group, an ethylsulfinyl group, and a t-butylsulfinyl group. The substituent thereof is not particularly limited and, for example, the same substituents as those of the aryl group for X can be exemplified in a chemically acceptable range. Specific examples of the C₁₋₈ alkoxy group substituted with an unsubstituted or substituted C₁₋₈alkylsulfinyl group include a methylsulfinylmethoxy group, a methylsulfinyl-n-butoxy group, and a 1-methylsulfinylethoxy group.

Specific examples of the arylsulfinyl group of the C₁₋₈ alkoxy group substituted with an unsubstituted or substituted arylsulfinyl group for Q¹ include a phenylsulfenyl group. The substituent thereof is not particularly limited and, for example, the same substituents as those of the aryl group for X can be exemplified in a chemically acceptable range. Specific examples of the C₁₋₈ alkoxy group substituted with an unsubstituted or substituted arylsulfinyl group include a phenylsulfinylmethoxy group, a 2-phenylsulfinylethoxy group, a naphthylsulfinylmethoxy group, and a 1-phenylsulfenylethoxy group.

Specific examples of the alkylsulfonyl group of the C₁₋₈ alkoxy group substituted with an unsubstituted or substituted C₁₋₈ alkylsulfonyl group for Q¹ include a methylsulfonyl group, an ethylsulfonyl group, and a t-butylsulfonyl group. The substituent thereof is not particularly limited and, for example, the same substituents as those of the aryl group for X can be exemplified in a chemically acceptable range. Specific examples of the C₁₋₈ alkoxy group substituted with an unsubstituted or substituted C₁₋₈ alkylsulfonyl group include a methylsulfonylmethoxy group, a methylsulfonyl-n-butoxy group, and a 1-methylsulfonylethoxy group.

Specific examples of the arylsulfonyl group of the C₁₋₈ alkoxy group substituted with an unsubstituted or substituted arylsulfonyl group for Q¹ include a phenylsulfonyl group. The substituent thereof is not particularly limited and, for example, the same substituents as those of the aryl group for X can be exemplified in a chemically acceptable range. Specific examples of the C₁₋₈ alkoxy group substituted with an unsubstituted or substituted arylsulfonyl group include a phenylsulfonylmethoxy group, a 2-phenylsulfonylethoxy group, a naphthylsulfonylmethoxy group, and a 1-phenylsulfonylethoxy group.

Specific examples of the aralkyl group of the C₁₋₈ alkoxy group substituted with an amino group which is unsubstituted or substituted with an (unsubstituted or substituted aralkyl group) for Q¹ include a benzyl group, a phenethyl group, and a 1-naphthylmethyl group. The substituent thereof is not particularly limited and, for example, the same substituents as those of the aryl group for X can be exemplified in a chemically acceptable range. Specific examples of the C₁₋₈ alkoxy group substituted with an amino group which is unsubstituted or substituted with an (unsubstituted or substituted aralkyl group) include an aminomethoxy group, a 3-aminopropoxy group, a 6-aminohexyloxy group, a 1-aminoethoxy group, benzylaminomethoxy group, an N-benzyl-N-methylaminomethoxy group, and an N-benzyl-N-methoxycarbonylaminomethoxy group.

As the alkyl group of the C₁₋₈ alkoxy group which is substituted with an amino group substituted with an (unsubstituted or substituted alkyl group) for Q¹, for example, the same alkyl groups as those for X can be exemplified. The substituent thereof is not particularly limited and, for example, the same substituents as those of the aryl group for X can be exemplified in a chemically acceptable range. Specific examples of the C₁₋₈ alkoxy group which is substituted with an amino group substituted with an (unsubstituted or substituted alkyl group) include a methylaminomethoxy group, a 3-methylaminopropoxy group, a 6-methylaminohexyloxy group, a 1-methylaminoethoxy group, a dimethylaminomethoxy group, a 2-ethylaminoethoxy group, and an N-methyl-N-methoxycarbonylaminomethoxy group.

The substituent of the unsubstituted or substituted aryloxy group for Q¹ is not particularly limited, and the same substituents as those of the aryl group for X can be exemplified in a chemically acceptable range. Specific examples of the unsubstituted or substituted aryloxy group include a phenoxy group, a naphthyloxy group, a 4-chlorophenoxy group, a 4-methoxyphenoxy group, a 2,4-dichlorophenoxy group, and a 2-trifluoromethylphenoxy group.

As the C₁₋₈ alkyl group of the C₁₋₈ alkyl group substituted with a carboxyl group for Q¹, for example, the same substituents as those of the alkyl group for X can be exemplified. Hereinafter, specific examples of the C₁₋₈ alkoxy group are the same specific examples. Specific examples of the C₁₋₈ alkyl group substituted with a carboxyl group include a 2-carboxyethyl group and a 6-carboxyhexyl group.

Specific examples of the aralkyl group of the C₁₋₈ alkyl group substituted with an amino group which is unsubstituted or substituted with an (unsubstituted or substituted aralkyl group) for Q¹ include a benzyl group, a phenethyl group, and a 1-naphthylmethyl group. The substituent thereof is not particularly limited and, for example, the same substituents as those of the aryl group for X can be exemplified in a chemically acceptable range.

Specific examples of the C₁₋₈ alkyl group substituted with an amino group which is unsubstituted or substituted with an (unsubstituted or substituted aralkyl group) include an aminomethyl group, a 3-aminopropyl group, a 6-aminohexyl group, a 1-aminoethyl group, a benzylaminomethyl group, an N-benzyl-N-methylaminomethyl group, and an N-benzyl-N-methoxycarbonylaminomethyl group.

As the alkyl group of the C₁₋₈ alkyl group which is substituted with an amino group substituted with an (unsubstituted or substituted alkyl group) for Q¹, for example, the same alkyl groups as those for X can be exemplified. The substituent thereof is not particularly limited and, for example, the same substituents as those of the aryl group for X can be exemplified in a chemically acceptable range. Specific examples of the C₁₋₈ alkyl group which is substituted with an amino group substituted with an (unsubstituted or substituted alkyl group) include a methylaminomethyl group, a 3-methylaminopropyl group, a 6-methylaminohexyl group, a 1-methylaminoethyl group, a dimethylaminomethyl group, a 2-ethylaminoethyl group, and an N-methyl-N-methoxycarbonylaminomethyl group.

Specific examples of the aryloxy group of the C₁₋₈ alkyl group substituted with an unsubstituted or substituted aryloxy group for Q¹ include a phenoxy group and a naphthyloxy group. The substituent thereof is not particularly limited and, for example, the same substituents as those of the aryl group for X can be exemplified in a chemically acceptable range. Specific examples of the C₁₋₈ alkyl group substituted with an unsubstituted or substituted aryloxy group include a phenoxymethyl group, a naphthyloxymethyl group, a 2-phenoxyethyl group, and a 1-phenoxyethyl group.

Specific examples of the acyl group of the C₁₋₈ alkyl group substituted with an acyl group for Q¹ include a formyl group, an acetyl group, a propionyl group, a benzoyl group, a cyclohexylcarbonyl group, and a phthaloyl group. Specific examples of the acyl group of the C₁₋₈ alkyl group substituted with an acyl group include a 4-acetyl-n-butyl group, an acetylmethyl group, a 1-acetylethyl group, and a 3-benzoyl-n-propyl group.

As the heterocyclicoxy group of the C₁₋₈ alkyl group substituted with an unsubstituted or substituted heterocyclicoxy group for Q¹, for example, those in which an oxygen atom is bonded to the bonding position of those of the heterocyclic group for R can be exemplified. The substituent of the heterocycle is not particularly limited and, for example, the same substituents as those of the aryl group for X can be exemplified in a chemically acceptable range. Specific examples of the C₁₋₈ alkyl group substituted with an unsubstituted or substituted heterocyclicoxy group include a 2-pyridyloxymethyl group, a 2-(2-pyridyloxy)ethyl group, a 1-(2-pyridyloxy)ethyl group, a (1-(2-pyridyloxy)-1-methyl)ethyl group, a 3-pyridyloxymethyl group, a 2-oxazolyloxymethyl group, and a 4-piperazyloxymethyl group.

Among these, Q¹ is preferably an alkenyloxy group in which carbon attached to the oxygen atom is tertiary carbon, such as a 1,1-dimethyl-2-propenyloxy group, an alkynyloxy group in which carbon attached to the oxygen atom is tertiary carbon, such as a 1,1-dimethyl-2-butynyloxy group, a C₁₋₈ alkoxy group substituted with an alkoxycarbonylamino group, a C₁₋₈ alkoxy group substituted with a C₃₋₈ cycloalkyl group, a C₁₋₈ branched alkoxy group substituted with an unsubstituted aryl group, a C₁₋₈ alkoxy group substituted with a substituted aryl group, a C₁₋₈ alkoxy group substituted with a substituted or unsubstituted heterocyclic group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted C₁₋₈ alkoxy group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted aryloxy group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted aralkyloxy group, a C₂₋₈ alkynyloxy group substituted with an unsubstituted or substituted aryl group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted C₁₋₈ alkylthio group, a C₁₋₈ alkoxy group substituted with a substituted or unsubstituted arylthio group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted C₁₋₈ alkylsulfinyl group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted arylsulfinyl group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted C₁₋₈ alkylsulfonyl group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted arylsulfonyl group, a C₁₋₈ alkoxy group substituted with an amino group which is unsubstituted or substituted with an (unsubstituted or substituted alkyl group), a C₁₋₈ alkoxy group which is substituted with an amino group substituted with an (unsubstituted or substituted aralkyl group), an unsubstituted or substituted aryloxy group, a C₁₋₈ alkyl group substituted with a carboxyl group, a C₁₋₈ alkyl group substituted with an amino group which is unsubstituted or substituted with an (unsubstituted or substituted aralkyl group), a C₁₋₈ alkyl group which is substituted with an amino group substituted with an (unsubstituted or substituted alkyl group), a C₁₋₈ alkyl group substituted with an unsubstituted or substituted aryloxy group, an alkyl group substituted with an acyl group, or an alkyl group substituted with an unsubstituted or substituted heterocyclicoxy group, and more preferably an alkenyloxy group in which carbon attached to the oxygen atom is tertiary carbon, such as a 1,1-dimethyl-2-propenyloxy group, an alkynyloxy group in which carbon attached to the oxygen atom is tertiary carbon, such as a 1,1-dimethyl-2-butynyloxy group, a C₁₋₈ alkoxy group substituted with a C₃₋₈ cycloalkyl group, a C₁₋₈ branched alkoxy group substituted with an unsubstituted aryl group, a C₁₋₈ alkoxy group substituted with a substituted aryl group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted heterocyclic group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted C₁₋₈ alkoxy group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted aryloxy group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted aralkyloxy group, a C₂₋₈ alkynyloxy group substituted with an unsubstituted or substituted aryl group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted C₁₋₈ alkylthio group, a C₁₋₈ alkoxy group substituted with an amino group which is unsubstituted or substituted with an (unsubstituted or substituted alkyl group), a C₁₋₈ alkoxy group which is substituted with an amino group substituted with an (unsubstituted or substituted aralkyl group), a C₁₋₈ alkyl group substituted with an amino group which is unsubstituted or substituted with an (unsubstituted or substituted aralkyl group), a C₁₋₈ alkyl group which is substituted with an amino group substituted with an (unsubstituted or substituted alkyl group), a C₁₋₈ alkyl group substituted with an unsubstituted or substituted aryloxy group, a C₁₋₈ alkyl group substituted with an acyl group, or a C₁₋₈ alkyl group substituted with an unsubstituted or substituted heterocyclicoxy group.

Furthermore, the alkenyloxy group in which carbon attached to the oxygen atom is tertiary carbon, such as a 1,1-dimethyl-2-propenyloxy group is preferably a 1,1-dialkyl-substituted alkenyl group, the alkynyloxy group in which carbon attached to the oxygen atom is tertiary carbon, such as a 1,1-dimethyl-2-butynyloxy group is preferably a 1,1-dialkyl-substituted alkynyloxy group, the C₁₋₈ alkoxy group substituted with a C₃₋₈ cycloalkyl is preferably a C₃₋₆ cycloalkyl C₁₋₂ alkyl group, the C₁₋₈ branched alkoxy group substituted with an unsubstituted aryl group is preferably a C₁₋₄ branched alkoxy group substituted with an unsubstituted aryl group at the 1- or 2-position, the C₁₋₈ alkoxy group substituted with a substituted aryl group is preferably a C₁₋₄ alkoxy group which is substituted with an aryl group substituted with a cyano group, a halogen atom, an alkoxy group, an alkyl group, an aryl group, or an alkylsulfonyl group, more preferably a C₁₋₄ alkoxy group which is substituted with a substituted aryl group substituted at the 2- or 3-position of the aryl group, and still more preferably a C₁₋₄ alkyl group which is substituted with an aryl group substituted with a cyano group, a halogen atom, an alkoxy group, an alkyl group, an aryl group, or an alkylsulfonyl group at the 2- or 3-position, the C₁₋₈ alkoxy group substituted with an unsubstituted or substituted heterocyclic group is preferably a C₁₋₄ alkoxy group substituted with an unsubstituted or substituted aromatic heterocyclic group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted C₁₋₈ alkoxy group is preferably a C₁₋₄ alkoxy group substituted with an unsubstituted or substituted C₁₋₄ alkoxy group, the C₁₋₈ alkoxy group substituted with an unsubstituted or substituted aryloxy group is preferably a C₁₋₄ alkoxy group substituted with an unsubstituted or substituted phenoxy group, the C₁₋₈ alkoxy group substituted with an unsubstituted or substituted aralkyloxy group is preferably a C₁₋₄ alkoxy group substituted with an unsubstituted or substituted benzyloxy group, the C₂₋₈ alkynyloxy group substituted with an unsubstituted or substituted aryl group is preferably a 1,1-dialkyl-substituted C₂₋₈ alkynyloxy group substituted with an unsubstituted or substituted phenyl group, the C₁₋₈ alkoxy group substituted with an unsubstituted or substituted C₁₋₈ alkylthio group is preferably a C₁₋₄ alkoxy group substituted with an unsubstituted or substituted C₁₋₄ alkylthio group, the C₁₋₈ alkoxy group substituted with an amino group which is unsubstituted or substituted with an (unsubstituted or substituted alkyl group) is preferably a C₁₋₄ alkoxy group substituted with an amino group which is unsubstituted or substituted with an (unsubstituted or substituted alkyl group), the C₁₋₈ alkoxy group which is substituted with an amino group substituted with an (unsubstituted or substituted aralkyl group) is preferably C₁₋₄ alkoxy group which is substituted with an amino group substituted with an (unsubstituted or substituted (benzyl group or phenethyl group)), the C₁₋₈ alkyl group substituted with an amino group which is unsubstituted or substituted with an (unsubstituted or substituted aralkyl group) is preferably a C₁₋₄ alkyl group substituted with an amino group which is unsubstituted or substituted with an (unsubstituted or substituted (benzyl group or phenethyl group)), the C₁₋₈ alkyl group which is substituted with an amino group substituted with an (unsubstituted or substituted alkyl group) is preferably a C₁₋₄ alkyl group which is substituted with an amino group substituted with an (unsubstituted or substituted alkyl group), the C₁₋₈ alkyl group substituted with an unsubstituted or substituted aryloxy group is preferably a C₁₋₄ alkyl group substituted with an unsubstituted or substituted phenoxy group, the C₁₋₈ alkyl group substituted with an acyl group is preferably a C₁₋₄ alkyl group substituted with a formyl group or an alkylcarbonyl group, or the C₁₋₈ alkyl group substituted with an unsubstituted or substituted heterocyclicoxy group is preferably a C₁₋₄ alkyl group substituted with an unsubstituted or substituted aromatic heterocyclicoxy group.

When n2 is 1 and R is a halogen atom, Z represents a hydrogen atom, an amino group, or a group represented by formula: Q²C(═O)NH— (in which Q² represents a hydrogen atom, a C₁₋₈ haloalkyl group, a C₂₋₈ alkenyl group, a C₂₋₈ haloalkenyl group, a C₂₋₈ alkynyl group, a C₂₋₈ haloalkynyl group, a C₁₋₈ alkoxy group, a C₁₋₈ haloalkoxy group, a C₂₋₈ alkenyloxy group, a C₂₋₈ haloalkenyloxy group, a C₂₋₈ alkynyloxy group, a C₂₋₈ haloalkynyloxy group, a C₃₋₈ cycloalkyl group, a C₃₋₈ cycloalkyloxy group, a C₁₋₈ alkylamino group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted amino group, a C₁₋₈ alkoxy group substituted with a C₃₋₈ cycloalkyl group, an unsubstituted or substituted aralkyloxy group, a C₁₋₈ alkoxy group substituted with a substituted or unsubstituted heterocyclic group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted C₁₋₈ alkoxy group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted aryloxy group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted aralkyloxy group, a C₂₋₈ alkynyloxy group substituted with an unsubstituted or substituted aryl group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted C₁₋₈ alkylthio group, a C₁₋₈ alkoxy group substituted with a substituted or unsubstituted arylthio group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted C₁₋₈ alkylsulfinyl group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted arylsulfinyl group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted C₁₋₈ alkylsulfonyl group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted arylsulfonyl group, an unsubstituted or substituted aryloxy group, a C₁₋₈ alkyl group substituted with a carboxyl group, a C₁₋₈ alkyl group substituted with an unsubstituted or substituted amino group, a C₁₋₈ alkyl group substituted with an unsubstituted or substituted aryloxy group, a C₁₋₈ alkyl group substituted with an unsubstituted or substituted C₁₋₈ alkylthio group, a C₁₋₈ alkyl group substituted with an unsubstituted or substituted alkoxy group, a C₁₋₈ alkyl group substituted with an acyl group, or a C₁₋₈ alkyl group substituted with an unsubstituted or substituted heterocyclicoxy group).

Specific examples of the C₁₋₈ haloalkyl group, the C₂₋₈ haloalkenyl group, the C₂₋₈ alkynyl group, the C₂₋₈ haloalkynyl group, the C₁₋₈ haloalkoxy group, the C₂₋₈ alkenyloxy group, the C₂₋₈ haloalkenyloxy group, the C₂₋₈ alkynyloxy group, the C₂₋₈ haloalkynyloxy group, the C₁₋₈ alkoxy group substituted with an C₃₋₈ cycloalkyl group, the C₁₋₈ alkoxy group substituted with a substituted or unsubstituted heterocyclic group, the C₁₋₈ alkoxy group substituted with an unsubstituted or substituted C₁₋₈ alkoxy group, the C₁₋₈ alkoxy group substituted with an unsubstituted or substituted aryloxy group, the C₁₋₈ alkoxy group substituted with an unsubstituted or substituted aralkyloxy group, the C₂₋₈ alkynyloxy group substituted with an unsubstituted or substituted aryl group, the C₁₋₈ alkoxy group substituted with an unsubstituted or substituted C₁₋₈ alkylthio group, the C₁₋₈ alkoxy group substituted with an unsubstituted or substituted arylthio group, the C₁₋₈ alkoxy group substituted with an unsubstituted or substituted C₁₋₈alkylsulfinyl group, the C₁₋₈ alkoxy group substituted with an unsubstituted or substituted arylsulfinyl group, the C₁₋₈ alkoxy group substituted with an unsubstituted or substituted C₁₋₈ alkylsulfonyl group, the C₁₋₈ alkoxy group substituted with an unsubstituted or substituted arylsulfonyl group, the unsubstituted or substituted aryloxy group, the C₁₋₈ alkyl group substituted with a carboxyl group, the C₁₋₈ alkyl group substituted with an unsubstituted or substituted aryloxy group, the C₁₋₈ alkyl group substituted with an acyl group, the or C₁₋₈ alkyl group substituted with an unsubstituted or substituted heterocyclicoxy group for Q² include the same specific examples as those of Q¹.

Specific examples of the C₃₋₈ cycloalkyl group for Q² include a cyclopropyl group, a cyclohexyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group.

Specific examples of the C₃₋₈ cycloalkyloxy group for Q² include a cyclopropyloxy group, a cyclohexyloxy group, a cyclobutyloxy group, a cyclopentyloxy group, a cyclohexyloxy group, a cycloheptyloxy group, and a cyclooctyloxy group.

Specific examples of the C₁₋₈ alkylamino group for Q² include a methylamino group, a diethylamino group, an ethylmethylamino group, a di n-heptylamino group, and a t-butylamino group.

The substituent of the amino group of the C₁₋₈ alkoxy group substituted with an unsubstituted or substituted amino group for Q² is not particularly limited and, for example, the same substituents as those of the aryl group for X can be exemplified in a chemically acceptable range. Specific examples of the C₁₋₈ alkoxy group substituted with an unsubstituted or substituted amino group include a 2-aminoethoxy group, a 6-aminohexyloxy group, an N-acetylaminomethoxy group, a 2-(N-acetylamino)ethoxy group, a 1-(N-acetylamino)ethoxy group, a 2-(N-acetyl-N-methylamino)ethoxy group, a 2-(N-benzoyl)aminoethoxy group, an N-methoxycarbonylaminomethoxy group, an N-t-butoxycrbonylaminomethoxy group, a 2-(N-ethoxycarbonylamino)ethoxy group, and a 2-(N-t-butoxycarbonyl-N-benzylamino)ethoxy group.

Specific examples of the aralkyloxy group of the unsubstituted or substituted aralkyloxy group for Q² include a benzyloxy group, a phenethyloxy group, and a 1-naphthylmethoxy group. The substituent thereof is not particularly limited and, for example, the same substituents as those of the aryl group for X can be exemplified in a chemically acceptable range. Specific examples of the unsubstituted or substituted aralkyloxy group include a benzyloxy group, a phenethyloxy group, a 1-phenylethoxy group, a 1-phenyl-1-methylethoxy group, a 2-phenyl-1-methylethoxy group, a 2-methylphenylmethoxy group, a 3-methylphenylmethoxy group, a 4-chlorophenylmethoxy group, a 1-(4-chlorophenyl)ethoxy group, a 3-chlorophenylmethoxy group, a 2-methoxyphenylmethoxy group, a 3-methoxyphenylmethoxy group, a 4-methylsulfonylphenylmethoxy group, and a 3-phenylphenylmethoxy group.

Specific examples of the alkylthio group of the C₁₋₈ alkyl group substituted with an unsubstituted or substituted C₁₋₈ alkylthio group for Q² include a methylthio group, an ethylthio group, an n-propylthio group, an isopropylthio group, an n-butylthio group, an isobutylthio group, an s-butylthio group, and a t-butylthio group. The substituent is not particularly limited and, for example, the same substituents as those of the aryl group for X can be exemplified in a chemically acceptable range. Specific examples of the C₁₋₈ alkyl group substituted with an unsubstituted or substituted C₁₋₈ alkylthio group include a methylthiomethyl group, a methylthio-n-butyl group, and a 1-methylthioethyl group.

As the alkoxy group of the C₁₋₈ alkyl group substituted with an unsubstituted or substituted alkoxy group for Q², for example, the same alkoxy groups as those for X can be exemplified. The substituent thereof is not particularly limited and, for example, the same substituents as those of the aryl group for X can be exemplified in a chemically acceptable range. Specific examples of the C₁₋₈ alkyl group substituted with an unsubstituted or substituted alkoxy group include a methoxymethyl group, an ethoxymethyl group, a 2-isopropoxyethyl group, an n-propoxyethyl group, a t-butoxy-1-butyl group, a 2-(2-methoxyethoxy)ethyl group, a 2-trifluoromethoxyethyl group, and a 2-pentafluoroethoxyethyl group.

Among these, Z is preferably a group represented by formula: Q²C(═O)NH—, and Q² is preferably a C₂₋₈ haloalkenyl group, a C₂₋₈ alkynyl group, a C₂₋₈ haloalkynyl group, a C₁₋₈ haloalkoxy group, a C₂₋₈ alkenyloxy group, a C₂₋₈ haloalkenyloxy group, a C₂₋₈ alkynyloxy group, a C₂₋₈ haloalkynyloxy group, a C₁₋₈ alkoxy group substituted with an amino group which is unsubstituted or substituted with an (unsubstituted or substituted alkyl group), a C₁₋₈ alkoxy group which is substituted with an amino group substituted with an (unsubstituted or substituted aralkyl group), a C₁₋₈ alkoxy group substituted with an alkoxycarbonylamino group, a C₁₋₈ alkoxy group substituted with a C₃₋₈ cycloalkyl group, a C₁₋₈ branched alkoxy group substituted with an unsubstituted aryl group, a C₁₋₈ alkoxy group substituted with a substituted aryl group, a C₁₋₈ alkoxy group substituted with a substituted or unsubstituted heterocyclic group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted C₁₋₈ alkoxy group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted aryloxy group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted aralkyloxy group, a C₂₋₈ alkynyloxy group substituted with an unsubstituted or substituted aryl group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted C₁₋₈ alkylthio group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted arylthio group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted C₁₋₈ alkylsulfinyl group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted arylsulfinyl group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted C₁₋₈ alkylsulfonyl group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted arylsulfonyl group, an unsubstituted or substituted aryloxy group, a C₁₋₈ alkyl group substituted with a carboxyl group, a C₁₋₈ alkyl group which is substituted with an amino group substituted with an (unsubstituted or substituted alkyl group), a C₁₋₈ alkyl group substituted with an amino group which is unsubstituted or substituted with an (unsubstituted or substituted aralkyl group), a C₁₋₈ alkyl group substituted with an unsubstituted or substituted aryloxy group, a C₁₋₈ alkyl group substituted with an amino group, or a C₁₋₈ alkyl group substituted with an unsubstituted or substituted heterocyclicoxy group, and more preferably an alkenyloxy group, in which carbon attached to the oxygen atom is tertiary carbon, such as a 1,1-dimethyl-2-propenyloxy group, an alkynyloxy group in which carbon attached to the oxygen atom is tertiary carbon, such as a 1,1-dimethyl-2-butynyloxy group, a C₁₋₈ alkoxy group substituted with a C₃₋₈ cycloalkyl group, a C₁₋₈ branched alkoxy group substituted with an unsubstituted aryl group, a C₁₋₈ alkoxy group substituted with a substituted aryl group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted heterocyclic group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted C₁₋₈ alkoxy group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted aryloxy group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted aralkyloxy group, a C₂₋₈ alkynyloxy group substituted with an unsubstituted or substituted aryl group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted C₁₋₈ alkylthio group, a C₁₋₈ alkoxy group substituted with an amino group which is unsubstituted or substituted with an (unsubstituted or substituted alkyl group), a C₁₋₈ alkoxy group which is substituted with an amino group substituted with an (unsubstituted or substituted aralkyl group), a C₁₋₈ alkyl group substituted with an amino group which is unsubstituted or substituted with an (unsubstituted or substituted aralkyl group), a C₁₋₈ alkyl group which is substituted with an amino group substituted with an (unsubstituted or substituted alkyl group), a C₁₋₈ alkyl group substituted with an unsubstituted or substituted aryloxy group, a C₁₋₈ alkyl group substituted with an acyl group, or a C₁₋₈ alkyl group substituted with an unsubstituted or substituted heterocyclicoxy group.

As more preferred above functional groups, the same as those for Q¹ can be exemplified.

When n2 is 1 or more and at least one R is a cyano group, a nitro group, a hydroxyl group, a thiol group, a formyl group, a carboxyl group, an unsubstituted or substituted amino group, an unsubstituted or substituted C₁₋₈ alkyl group, an unsubstituted or substituted C₂₋₈ alkenyl group, an unsubstituted or substituted C₂₋₈ alkynyl group, an unsubstituted or substituted aryl group, an unsubstituted or substituted heterocyclic group, OR¹, S(O)_(m)R¹, COR¹, or CO₂R¹, or n2 is 2 or more and at least two R(s) are halogen atoms, Z represents a hydrogen atom, an amino group, or a group represented by formula: Q³C(═O)NH— (in which Q³ represents a hydrogen atom, a C₁₋₈ alkyl group, a C₁₋₈ haloalkyl group, a C₂₋₈ alkenyl group, a C₂₋₈ haloalkenyl group, a C₂₋₈ alkynyl group, a C₂₋₈ haloalkynyl group, a C₁₋₈ alkoxy group, a C₁₋₈ haloalkoxy group, a C₂₋₈ alkenyloxy group, a C₂₋₈ haloalkenyloxy group, a C₂₋₈ alkynyloxy group, a C₂₋₈ haloalkynyloxy group, a C₃₋₈ cycloalkyl group, a C₃₋₈ cycloalkyloxy group, a C₁₋₈ alkylamino group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted amino group, a C₁₋₈ alkoxy group substituted with a C₃₋₈ cycloalkyl group, an unsubstituted or substituted aralkyloxy group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted heterocyclic group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted C₁₋₈ alkoxy group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted aryloxy group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted aralkyloxy group, a C₂₋₈ alkynyloxy group substituted with an unsubstituted or substituted aryl group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted C₁₋₈ alkylthio group, a C₁₋₈ alkoxy group substituted with a substituted or unsubstituted arylthio group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted C₁₋₈ alkylsulfinyl group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted arylsulfinyl group, C₁₋₈ alkoxy group substituted with an unsubstituted or substituted C₁₋₈ alkylsulfonyl group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted arylsulfonyl group, an unsubstituted or substituted aryloxy group, a C₁₋₈ alkyl group substituted with a carboxyl group, a C₁₋₈ alkyl group substituted with an unsubstituted or substituted amino group, a C₁₋₈ alkyl group substituted with an unsubstituted or substituted aryloxy group, a C₁₋₈ alkyl group substituted with an unsubstituted or substituted C₁₋₈ alkylthio group, a C₁₋₈ alkyl group substituted with an unsubstituted or substituted alkoxy group, a C₁₋₈ alkyl group substituted with an acyl group, or a C₁₋₈ alkyl group substituted with an unsubstituted or substituted heterocyclicoxy group).

As the C₁₋₈ alkyl group for Q³, for example, the same as those of C₁₋₈ alkyl group for X can be exemplified.

As specific examples of other functional group contained in Q³, the same as those for Q² can be exemplified.

Among these, formula: Q³C(═O)NH— is preferable. Among these, Q³ is preferably a C₁₋₈ alkyl group, a C₁₋₈ haloalkyl group, a C₂₋₈ alkenyl group, a C₁₋₈ alkoxy group, a C₂₋₈ alkenyloxy group, a C₂₋₈ alkynyloxy group, a C₃₋₈ cycloalkyl group, a C₃₋₈ cycloalkyloxy group, a C₁₋₈ alkylamino group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted amino group, a C₁₋₈ alkoxy group substituted with a C₃₋₈ cycloalkyl group, an unsubstituted or substituted aralkyloxy group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted heterocyclic group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted C₁₋₈ alkoxy group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted aryloxy group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted aralkyloxy group, a C₂₋₈ alkynyloxy group substituted with an unsubstituted or substituted aryl group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted C₁₋₈ alkylthio group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted arylthio group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted C₁₋₈ alkylsulfinyl group, C₁₋₈ alkoxy group substituted with an unsubstituted or substituted arylsulfinyl group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted C₁₋₈ alkylsulfonyl group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted arylsulfonyl group, an unsubstituted or substituted aryloxy group, a C₁₋₈ alkyl group substituted with a carboxyl group, a C₁₋₈ alkyl group substituted with an unsubstituted or substituted amino group, a C₁₋₈ alkyl group substituted with an unsubstituted or substituted aryloxy group, a C₁₋₈ alkyl group substituted with an unsubstituted or substituted C₁₋₈ alkylthio group, a C₁₋₈ alkyl group substituted with an unsubstituted or substituted alkoxy group, a C₁₋₈ alkyl group substituted with an acyl group, or a C₁₋₈ alkyl group substituted with an unsubstituted or substituted heterocyclicoxy group, and still more preferably the same as those for Q¹.

In formula (5), R¹¹ represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, a hydroxyl group, a thiol group, an unsubstituted or substituted amino group, an unsubstituted or substituted C₁₋₈ alkyl group, an unsubstituted or substituted C₂₋₈ alkenyl group, an unsubstituted or substituted C₂₋₈ alkynyl group, an unsubstituted or substituted aryl group, an unsubstituted or substituted heterocyclic group, OR¹, S(O)_(m)R¹, COR¹, or CO₂R¹.

R¹ is the same as defined above.

When R¹¹ is a hydrogen atom, Z¹¹ represents a group represented by formula: Q¹C(═O)NH— (in which Q¹ is the same as defined above).

When R¹¹ is a halogen atom, Z¹¹ represents a hydrogen atom, an amino group, or a group represented by formula: Q²C(═O)NH— (in which Q² is the same as defined above).

When R¹¹ is a cyano group, a nitro group, a hydroxyl group, a thiol group, an unsubstituted or substituted amino group, an unsubstituted or substituted C₁₋₈ alkyl group, an unsubstituted or substituted C₂₋₈ alkenyl group, an unsubstituted or substituted C₂₋₈ alkynyl group, an unsubstituted or substituted aryl group, an unsubstituted or substituted heterocyclic group, OR¹, S(O)_(m)R¹, COR¹, or CO₂R¹, Z¹¹ represents a hydrogen atom, an amino group, or a group represented by formula: Q³C(═O)NH— (in which Q³ is the same as defined above).

As the specific examples of R¹¹, the same specific examples as those for R in formula (4) can be exemplified. As the specific examples of Z¹¹, the same specific examples as those for Z in formula (4) can be exemplified.

As preferred Z¹¹, the same as those for Z can be exemplified.

Stereoisomers of (E) and (Z) isomers, based on the double bond of carbon-nitrogen in the oxime moiety, exist in the tetrazoyloxime derivative represented by formula (1). These two stereoisomers and a mixture thereof are included in the present invention. The synthesized product is usually obtained in the form of the (Z) isomer only, or a mixture of (E) and (Z) isomers. Each of (E) and (Z) isomers can be isolated by separation and purification, known methods such as silica gel chromatography. Both (Z) and (E) isomers have activity and (Z) isomer is particularly preferable.

Salts of the compound represented by formula (1) are not particularly limited as long as they are agriculturally or horiculturally acceptable salts. Examples of the salts include salts of inorganic acids, such as hydrochloride, nitrate, sulfate, and phosphate; and salts of organic acids, such as acetate, lactate, propionate, and benzoate.

(Preparation Method)

The tetrazoyloxime derivative represented by formula (1) can be prepared, for example, by the method described in pamphlet of WO 03/016303.

(In the above formulas, A, X, Het and n1 is the same as defined above, and L represents a leaving group such as halogen atom.)

That is to say, the compound represented by formula (1) of the present invention can be obtained by reacting an oxime compound represented by formula (6) with a compound represented by formula (7) in the presence of a base.

As the base used for the reaction, inorganic bases such as sodium hydroxide, potassium hydroxide, sodium hydride, sodium carbonate, and potassium carbonate; and organic bases such as triethylamine, 4-(dimethylamino)pyridine, and pyridine can be used. These bases can be used alone, or two or more kinds of them can be used in combination.

The used amount of the base is usually from 0.01 to 100 mol, and preferably from 0.1 to 5 mol, per mol of the compound represented by formula (6).

This reaction can be performed in the presence or absence of a solvent.

The solvent to be used is not particularly limited as long as it is a solvent which is inert to the present reaction. Examples of the solvent include hydrocarbon-based solvents such as pentane, hexane, heptane, benzene, toluene, and xylene; halogen-based solvents such as dichloromethane, chloroform, and hydrocarbon tetrachloride; nitrile-based solvents such as acetonitrile and propionitrile; ether-based solvents such as diethylether, dioxane, and tetrahydrofuran; amide-based solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, and N-methyl pyrrolidone; sulfoxide-based solvents such as dimethyl sulfoxide; water; and a mixed solvent thereof.

The reaction temperature of the reaction is usually within a range from −70° C. to +200° C., and preferably from −20° C. to +100° C.

The reaction time varies depending on the reaction scale, but is usually within a range from 30 minutes to 24 hours.

Salts of the compound represented by formula (1) can be prepared by reacting the compound represented by formula (1) with an acid by a conventional method.

After completion of any reaction, the objective compound represented by formula (1) and a salt thereof can be isolated by performing a usual work-up operation. If it is necessary to purify the product, conventionally known purification means such as distillation, recrystallization or column chromatography can be employed.

Specific examples of the thus prepared tetrazoyloxime derivative represented by formula (1) of the present invention are shown in Table 1 to Table 4 shown below. Abbreviations in the tables have meanings shown below. Me: methyl, Et: ethyl, Pr: propyl, Bu: butyl, Hex: hexyl, i: iso, n: normal, s: secondary, t: tertiary, c: cyclo, Ph: phenyl, and Py: pyridyl

TABLE 1

mp No Z R_(n2) (X)_(n1) ° C. 1-1 H 4-Me — 1-2 NH₂ 4-Me — 1-3 NH₂ 4-Bu-t — 1-4 NH₂ 4-OC₂H₅ — 1-5 NH₂ 5-CH₃ — 1-6 NH₂ 4-OCH₃ — 1-7 NH₂ 4-C₂H₅ — 1-8 NHCHO 4-Me — 1-9 NHCOCH₃ 4-Me — 1-10 NHCOC₂H₅ 4-Me — 1-11 NHCOPr-n 4-Me — 1-12 NHCOPr-i 4-Me — 1-13 NHCOBu-n 4-Me — 1-14 NHCOBu-i 4-Me — 1-15 NHCOBu-s 4-Me — 1-16 NHCOBu-t 4-Me — 1-17 NHCOBu-t 4-OMe — 1-18 NHCOCH₂CF₃ 4-Me — 1-19 NHCOC₂F₅ 4-Me — 1-20 NHCOCH₂CH₂F 4-Me — 1-21 NHCOC(CH₃)₂CF₃ 4-Me — 1-22 NHCOCH₂CH₂CF₃ 4-Me — 1-23 NHCOCH₂C₂F₅ 4-Me — 1-24 NHCOCH₂CH═CH₂ 4-Me — 1-25 NHCOCH₂CH═CMe₂ 4-Me — 1-26 NHCOC(CH₃)₂CH═CH₂ 4-Me — 1-27 NHCOC(CH₃)₂CH═CHCH₃ 4-Me — 1-28 NHCOCH₂CH═CHCl 4-Me — 1-29 NHCOCH₂CH═CHCF₃ 4-Me — 1-30 NHCOCH₂CI═CI₂ 4-Me — 1-31 NHCO(1,1-dimethyl-2- 4-Me — propynyl) 1-32 NHCO(2-butynyl) 4-Me — 1-33 NHCO(1,1-dimethyl-2- 4-Me — butynyl) 1-34 NHCO(1,1-dimethyl-2- 4-Me — pentynyl) 1-35 NHCO(1-propynyl) 4-Me — 1-36 NHCO(1,1-dimethyl-3-Iodo- 4-Me — 2-pentynyl) 1-37 NHCO(4,4,4-trifluoro-2- 4-Me — butynyl) 1-38 NHCOPr-c 4-Me — 1-39 NHCOHex-c 4-Me — 1-40 NHCO(CH₂)₄CO₂H 4-Me — 1-41 NHCOCH₂CH₂NHCO₂Bu-t 4-Me — 1-42 NHCOCH₂CH₂NHCO₂Et 4-Me — 1-43 NHCOCH₂CH₂CH₂NHCOCH₃ 4-Me — 1-44 NHCOCH₂CH₂CH₂NHMe₂ 4-Me — 1-45 NHCOCH₂CH₂N(Me)COCH₃ 4-Me — 1-46 NHCOCH₂CH₂NHCOPh 4-Me — 1-47 NHCOCH₂CH₂N(Me)COPh 4-Me — 1-48 NHCOCH₂CH₂NHPh 4-Me — 1-49 NHCO(CH₂)₄NH₂ 4-Me — 1-50 NHCOCH₂NHCH₂Ph 4-Me — 1-51 NHCOCH₂N(CH₂Ph)(CO₂Bu-t) 4-Me — 1-52 NHCOCH₂CH₂OC₆H₄Cl-4 4-Me — 1-53 NHCOCH₂OPh 4-Me — 1-54 NHCOCH₂OC₆H₄F-3 4-Me — 1-55 NHCOCH₂OC₆H₄OCF₃-3 4-Me — 1-56 NHCO(CH₂)₄SMe 4-Me — 1-57 NHCOCH₂CH₂OEt 4-Me — 1-58 NHCOCH₂CH₂OPr-i 4-Me — 1-59 NHCOCH₂CH₂OBu-i 4-Me — 1-60 NHCOCH₂CH₂OCH₂CH₂OMe 4-Me — 1-61 NHCO₂CH₃ 4-Me — 1-62 NHCO₂C₂H₅ 4-Me — 1-63 NHCO₂Pr-n 4-Me — 1-64 NHCO₂Pr-i 4-Me — 1-65 NHCO₂Bu-n 4-Me — 1-66 NHCO₂Bu-i 4-Me — 1-67 NHCO₂Bu-s 4-Me — 1-68 NHCO₂Bu-t 4-i-Pr — 68-70 1-69 NHCO₂Bu-t 5-Me — 60-63 1-70 NHCO₂Bu-t 4-t-Bu — 68-69 1-71 NHCO₂Bu-t 4-Me — 1-72 NHCO₂Bu-t 4-Et — 42-46 1-73 NHCO₂Bu-t 4-CH═CH2 — 1-74 NHCO₂Bu-t 4-OMe — 151-153 1-75 NHCO₂Bu-t 4-OEt — 54-55 1-76 NHCO₂Bu-t 4-OCH₂CH₂OEt — <50 1-77 NHCO₂Bu-t 4-OPr-i — 1-78 NHCO₂Bu-t 4-OBu-n — 1-79 NHCO₂Bu-t 4-SMe — 142-144 1-80 NHCO₂Bu-t 4-SOMe — 86-88 1-81 NHCO₂Bu-t 4-SO₂Me — 117-118 1-82 NHCO₂Bu-t 4-NMe₂ — 1-83 NHCO₂Bu-t 4-N(Me)(CO₂Bu-t) — 1-84 NHCO₂Bu-t 5-CN — 68-72 1-85 NHCO₂Bu-t 4-CN — 70-75 1-86 NHCO₂Bu-t 4-morphorino — 1-87 NHCO₂Bu-t 5-Ph —  99-102 1-88 NHCO₂Bu-t 5-CO₂C₂H₅ — 74-77 1-89 NHCO₂Bu-t 5-CONHCH₃ — 1-90 NHCO₂Bu-t CF₃ — 1-91 NHCO₂Bu-t 5-OH — 1-92 NHCO₂Bu-t 5-SH — 1-93 NHCO₂Bu-t 4-CH₂CI═CI₂ — 1-94 NHCO₂Bu-t 4-etynyl — 1-95 NHCO₂Bu-t 4-propargyl — 1-96 NHCO₂Bu-t 4-(3-iodo-2- — propynyl) 1-97 NHCO₂Bu-t 4-Ph — 1-98 NHCO₂Bu-t 4-C₆H₄OMe-4 — 1-99 NHCO₂Bu-t 4-(2-pyridyl) — 1-100 NHCO₂Bu-t 4-(4-CF₃-2- — oxazolyl) 1-101 NHCO₂Bu-t 4-(3-CF₃-5-Cl-2- — pyridyl) 1-102 NHCO₂Bu-t 4-pyrrolidino — 1-103 NHCO₂Bu-t 4-COMe — 1-104 NHCO₂Bu-t 4-CONHMe — 1-105 NHCO₂Bu-t 4-CONMe₂ — 1-106 NHCO₂Bu-t 4-COPr-c — 1-107 NHCO₂Bu-t 4-COPh — 1-108 NHCO₂Bu-t 4-COCH₂CH═CH₂ — 1-109 NHCO₂Bu-t 4-CO(propargyl) — 1-110 NHCO₂Bu-t 4-CO₂Me — 1-111 NHCO₂Bu-t 4-CO₂Ph — 1-112 NHCO₂Bu-t 4-CO₂CH₂CH═CH₂ — 1-113 NHCO₂Bu-t 4-CO₂(propargyl) — 1-114 NHCO₂Bu-t 4-Me 2-Cl 1-115 NHCO₂Bu-t 4-Me 3-Cl 1-116 NHCO₂Bu-t 4-Me 4-Cl 1-117 NHCO₂Bu-t 4-Me 2,4-Cl₂ 1-118 NHCO₂Bu-t 4-Me 3,5-Cl₂ 1-119 NHCO₂Bu-t 4-Me 3,4,5-Cl₃ 1-120 NHCO₂Bu-t 4-Me 2-Me 1-121 NHCO₂Bu-t 3,4-diMe — 1-122 NHCO₂Bu-t 3,5-diMe — 1-123 NHCO₂Bu-t 4,5-diMe — 1-124 NHCO₂Bu-t 3,4,5-triMe — 1-125 NHCO₂Bu-t 3-Cl-4-Me — 1-126 NHCO₂Bu-t 5-Cl-4-Me — 1-127 NHCO₂Bu-t 3,5-diCl-4-Me — 1-128 NHCO₂Bu-t 3,5-diCl — 1-129 NHCO₂Bu-t 3,4-diCl — 1-130 NHCO₂Bu-t 3,4-diF — 1-131 NHCO₂Bu-n 4-NH₂ — 1-132 NHCO₂Bu-n 4-NHCO₂Bu-t — 1-133 NHCO₂CH₂CF₃ 4-Me — 1-134 NHCO₂C₂F₅ 4-Me — 1-135 NHCO₂CH₂CH₂F 4-Me — 1-136 NHCO₂C(CH₃)₂CF₃ 4-Me — 1-137 NHCO₂CH₂CH₂CF₃ 4-Me — 1-138 NHCO₂CH₂C₂F₅ 4-Me — 1-139 NHCO₂CH₂CH═CH₂ 4-Me — 1-140 NHCO₂CH₂CH═CMe₂ 4-Me — 1-141 NHCO₂C(CH₃)₂CH═CH₂ 4-Me — 1-142 NHCO₂C(CH₃)₂CH═CH₃ 4-Me — 1-143 NHCO₂CH₂CH═CHCl 4-Me — 1-144 NHCO₂CH₂CH═CHCF₃ 4-Me — 1-145 NHCO₂CH₂CI═CI₂ 4-Me — 1-146 NHCO₂(1,1-dimethyl-2- 4-Me — propynyl) 1-147 NHCO₂(2-butynyl) 4-Me — 1-148 NHCO₂(1,1-dimethyl-2- 4-Me — butynyl) 1-149 NHCO₂(1,1-dimethyl-2- 4-Me — pentynyl) 1-150 NHCO₂(1-propynyl) 4-Me — 1-151 NHCO₂(1,1-dimethyl-3-Iodo- 4-Me — 2-pentynyl) 1-152 NHCO₂(4,4,4-trifluoro-2- 4-Me — butynyl) 1-153 NHCO₂Pr-c 4-Me — 1-154 NHCO₂Hex-c 4-Me — 1-155 NHCO₂CH₂CH₂NHCO₂Bu-t 4-Me — 1-156 NHCO₂CH₂CH₂NHCO₂Et 4-Me — 1-157 NHCO₂CH₂CH₂CH₂NHCOCH₃ 4-Me — 1-158 NHCO₂CH₂CH₂CH₂NHMe₂ 4-Me — 1-159 NHCO₂CH₂CH₂N(Me)COCH₃ 4-Me — 1-160 NHCO₂CH₂CH₂NHCOPh 4-Me — 1-161 NHCO₂CH₂CH₂N(Me)COPh 4-Me — 1-162 NHCO₂CH₂CH₂NHPh 4-Me — 1-163 NHCO₂(CH₂)₄NH₂ 4-Me — 1-164 NHCO₂CH₂NHCH₂Ph 4-Me — 1-165 NHCO₂CH₂N(CH₂Ph)(CO₂Bu-t) 4-Me — 1-166 NHCO₂CH₂C₃H₅-c 4-Me — 1-167 NHCO₂CH(CH₃)C₃H₅-c 4-Me — 1-168 NHCO₂CH₂C₆H₁₁-c 4-Me — 1-169 NHCO₂CH₂Ph 4-Me — 1-170 NHCO₂CH(CH₃)CH₂Ph 4-Me — 1-171 NHCO₂CH(CH₃)Ph 4-Me — 1-172 NHCO₂CH(CH₃)₂Ph 4-Me — 1-173 NHCO₂CH₂C₆H₄CF₃-4 4-Me — 1-174 NHCO₂CH₂C₆H₄CN-4 4-Me — 1-175 NHCO₂CH₂C₆H₄CN-3 4-Me — 1-176 NHCO₂CH₂C₆H₄Cl-4 4-Me — 1-177 NHCO₂CH₂C₆H₄Cl-3 4-Me — 1-178 NHCO₂CH₂C₆H₄OMe-3 4-Me — 1-179 NHCO₂CH₂C₆H₄OMe-2 4-Me — 1-180 NHCO₂CH₂C₆H₄Me-4 4-Me — 1-181 NHCO₂CH₂C₆H₄Me-3 4-Me — 1-182 NHCO₂CH₂C₆H₄Me-2 4-Me — 1-183 NHCO₂CH₂C₆H₄SO₂Me-4 4-Me — 1-184 NHCO₂CH₂C₆H₄SO₂Me-3 4-Me — 1-185 NHCO₂CH₂C₆H₄Ph-4 4-Me — 1-186 NHCO₂CH₂C₆H₄Ph-3 4-Me — 1-187 NHCO₂CH₂Py-2 4-Me — 1-188 NHCO₂CH₂(6-Me-2-Py) 4-Me — 1-189 NHCO₂C(CH₃)₂Py-4 4-Me — 1-190 NHCO₂CH₂(2-thiazolyl) 4-Me — 1-191 NHCO₂CH₂(2-benzthiazolyl) 4-Me — 1-192 NHCO₂CH₂CH₂OMe 4-Me — 1-193 NHCO₂CH₂CH₂OEt 4-Me — 1-194 NHCO₂CH₂CH₂OPr-i 4-Me — 1-195 NHCO₂CH₂CH₂OBu-i 4-Me — 1-196 NHCO₂CH₂CH₂OCH₂CH₂OMe 4-Me — 1-197 NHCO₂CH₂CH₂OEt 4-i-Pr — 1-198 NHCO₂CH₂CH₂OC₆H₄Cl-4 4-Me — 1-199 NHCOCH₂OPh 4-Me — 1-200 NHCOCH₂OC₆H₄F-3 4-Me — 1-201 NHCOCH₂OC₆H₄OCF₃-3 4-Me — 1-202 NHCO₂CH₂CH₂OCH₂Ph 4-Me — 1-203 NHCO₂CH₂CH₂OCH₂CH₂Ph 4-Me — 1-204 NHCO₂(1,1-dimethyl-3- 4-Me — phenyl-2-pentynyl) 1-205 NHCO₂(CH₂)₄SMe 4-Me — 1-206 NHCO₂(CH₂)₄SCF₃ 4-Me — 1-207 NHCO₂(CH₂)₄SPh 4-Me — 1-208 NHCO₂(CH₂)₄SOMe 4-Me — 1-209 NHCO₂(CH₂)₄SOCF₃ 4-Me — 1-210 NHCO₂(CH₂)₄SOPh 4-Me — 1-211 NHCO₂(CH₂)₄SO₂Me 4-Me — 1-212 NHCO₂(CH₂)₄SO₂CF₃ 4-Me — 1-213 NHCO₂(CH₂)₄SO₂Ph 4-Me — 1-214 NHCO₂Ph 4-Me — 1-215 NHCO₂C₆H₄OMe-4 4-Me — 1-216 NHCONHMe 4-Me — 1-217 NHCONHC₂H₅ 4-Me — 1-218 NHCONHPr-n 4-Me — 1-219 NHCONHBu-t 4-Me — 1-220 NHCONHBu-s 4-Me — 1-221 NHCONH(Hex-n) 4-Me — 1-222 H 4-Cl — 1-223 NH₂ 4-Cl — 1-224 NHCHO 4-Cl — 1-225 NHCOCH₂CF₃ 4-Cl — 1-226 NHCOC₂F₅ 4-Cl — 1-227 NHCOCH₂CH₂F 4-Cl — 1-228 NHCOC(CH₃)₂CF₃ 4-Cl — 1-229 NHCOCH₂CH₂CF₃ 4-Cl — 1-230 NHCOCH₂C₂F₅ 4-Cl — 1-231 NHCOCH₂CH═CH₂ 4-Cl — 1-232 NHCOCH₂CH═CMe₂ 4-Cl — 1-233 NHCOC(CH₃)₂CH═CH₂ 4-Cl — 1-234 NHCOC(CH₃)₂CH═CHCH₃ 4-Cl — 1-235 NHCOCH₂CH═CHCl 4-Cl — 1-236 NHCOCH₂CH═CHCF₃ 4-Cl — 1-237 CHCOCH₂CI═CI₂ 4-Cl — 1-238 NHCO(1,1-dimethyl-2- 4-Cl — propynyl) 1-239 NHCO(2-butynyl) 4-Cl — 1-240 NHCO(1,1-dimethyl-2- 4-Cl — butynyl) 1-241 NHCO(1,1-dimethyl-2- 4-Cl — pentynyl) 1-242 NHCO(1-propynyl) 4-Cl — 1-243 NHCO(1,1-dimethyl-3-Iodo- 4-Cl — 2-pentynyl) 1-244 NHCO(4,4,4-trifluoro-2- 4-Cl — butynyl) 1-245 NHCOPr-c 4-Cl — 1-246 NHCOHex-c 4-Cl — 1-247 NHCO(CH₂)₄CO₂H 4-Cl — 1-248 NHCOCH₂CH₂NHCO₂Bu-t 4-Cl — 1-249 NHCOCH₂CH₂NHCO₂Et 4-Cl — 1-250 NHCOCH₂CH₂CH₂NHCOCH₃ 4-Cl — 1-251 NHCOCH₂CH₂CH₂NHMe₂ 4-Cl — 1-252 NHCOCH₂CH₂N(Me)COCH₃ 4-Cl — 1-253 NHCOCH₂CH₂NHCOPh 4-Cl — 1-254 NHCOCH₂CH₂N(Me)COPh 4-Cl — 1-255 NHCOCH₂CH₂NHPh 4-Cl — 1-256 NHCO(CH₂)₄NH₂ 4-Cl — 1-257 NHCOCH₂NHCH₂Ph 4-Cl — 1-258 NHCOCH₂N(CH₂Ph)(CO₂Bu-t) 4-Cl — 1-259 NHCOCH₂CH₂OC₆H₄Cl-4 4-Cl — 1-260 NHCOCH₂OPh 4-Cl — 1-261 NHCOCH₂OC₆H₄F-3 4-Cl — 1-262 NHCOCH₂OC₆H₄OCF₃-3 4-Cl — 1-263 NHCO(CH₂)₄SMe 4-Cl — 1-264 NHCOCH₂CH₂OEt 4-Cl — 1-265 NHCOCH₂CH₂OPr-i 4-Cl — 1-266 NHCOCH₂CH₂OBu-i 4-Cl — 1-267 NHCOCH₂CH₂OCH₂CH₂OMe 4-Cl — 1-268 NHCO₂CH₃ 4-Cl — 1-269 NHCO₂C₂H₅ 4-Cl — 1-270 NHCO₂Pr-n 4-Cl — 1-271 NHCO₂Pr-i 4-Cl — 1-272 NHCO₂Bu-n 4-Cl — 1-273 NHCO₂Bu-i 4-Cl — 1-274 NHCO₂Bu-s 4-Cl — 1-275 NHCO₂Bu-t 4-Cl — 1-276 NHCO₂Bu-t 5-Br — 58-61 1-277 NHCO₂Bu-t 5-Cl — 38-41 1-278 NHCO₂Bu-t 4-Br — 1-279 NHCO₂Bu-t 4-Cl 2-Cl 1-280 NHCO₂Bu-t 4-Cl 3-Cl 1-281 NHCO₂Bu-t 4-Cl 4-Cl 1-282 NHCO₂Bu-t 4-Cl 2,4-Cl₂ 1-283 NHCO₂Bu-t 4-Cl 3,5-Cl₂ 1-284 NHCO₂Bu-t 4-Cl 3,4,5- Cl₃ 1-285 NHCO₂Bu-t 4-Cl 2-Me 1-286 NHCO₂CH₂CF₃ 4-Cl — 1-287 NHCO₂C₂F₅ 4-Cl — 1-288 NHCO₂CH₂CH₂F 4-Cl — 1-289 NHCO₂C(CH₃)₂CF₃ 4-Cl — 1-290 NHCO₂CH₂CH₂CF₃ 4-Cl — 1-291 NHCO₂CH₂C₂F₅ 4-Cl — 1-292 NHCO₂CH₂CH═CH₂ 4-Cl — 1-293 NHCO₂CH₂CH═CMe₂ 4-Cl — 1-294 NHCO₂C(CH₃)₂CH═CH₂ 4-Cl — 1-295 NHCO₂C(CH₃)₂CH═CHCH₃ 4-Cl — 1-296 NHCO₂CH₂CH═CHCl 4-Cl — 1-297 NHCO₂CH₂CH═CHCF₃ 4-Cl — 1-298 NHCO₂CH₂CI═CI₂ 4-Cl — 1-299 NHCO₂(1,1-dimethyl-2- 4-Cl — propynyl) 1-300 NHCO₂(2-butynyl) 4-Cl — 1-301 NHCO₂(1,1-dimethyl-2- 4-Cl — butynyl) 1-302 NHCO₂(1,1-dimethyl-2- 4-Cl — pentynyl) 1-303 NHCO₂(1-propynyl) 4-Cl — 1-304 NHCO₂(1,1-dimethyl-3-Iodo- 4-Cl — 2-pentynyl) 1-305 NHCO₂(4,4,4-trifluoro-2- 4-Cl — butynyl) 1-306 NHCO₂Pr-c 4-Cl — 1-307 NHCO₂Hex-c 4-Cl — 1-308 NHCO₂CH₂CH₂NHCO₂Bu-t 4-Cl — 1-309 NHCO₂CH₂CH₂NHCO₂Et 4-Cl — 1-310 NHCO₂CH₂CH₂CH₂NHCOCH₃ 4-Cl — 1-311 NHCO₂CH₂CH₂CH₂NMe₂ 4-Cl — 1-312 NHCO₂CH₂CH₂N(Me)COCH₃ 4-Cl — 1-313 NHCO₂CH₂CH₂NHCOPh 4-Cl — 1-314 NHCO₂CH₂CH₂N(Me)COPh 4-Cl — 1-315 NHCO₂CH₂CH₂NHPh 4-Cl — 1-316 NHCO₂(CH₂)₄NH₂ 4-Cl — 1-317 NHCO₂CH₂NHCH₂Ph 4-Cl — 1-318 NHCO₂CH₂N(CH₂Ph)(CO₂Bu-t) 4-Cl — 1-319 NHCO₂CH₂C₃H₅-c 4-Cl — 1-320 NHCO₂CH(CH₃)C₃H₅-c 4-Cl — 1-321 NHCO₂CH₂C₆H₁₁-c 4-Cl — 1-322 NHCO₂CH₂Ph 4-Cl — 1-323 NHCO₂CH₂Ph 5-Cl — 109-110 1-324 NHCO₂CH(CH₃)CH₂Ph 4-Cl — 1-325 NHCO₂CH(CH₃)Ph 4-Cl — 1-326 NHCO₂C(CH₃)₂Ph 4-Cl — 1-327 NHCO₂CH₂C₆H₄CF₃-4 4-Cl — 1-328 NHCO₂CH₂C₆H₄CN-4 4-Cl — 1-329 NHCO₂CH₂C₆H₄CN-3 4-Cl — 1-330 NHCO₂CH₂C₆H₄Cl-4 4-Cl — 1-331 NHCO₂CH₂C₆H₄Cl-3 4-Cl — 1-332 NHCO₂CH₂C₆H₄OMe-3 4-Cl — 1-333 NHCO₂CH₂C₆H₄OMe-2 4-Cl — 1-334 NHCO₂CH₂C₆H₄Me-4 4-Cl — 1-335 NHCO₂CH₂C₆H₄Me-3 4-Cl — 1-336 NHCO₂CH₂C₆H₄Me-2 4-Cl — 1-337 NHCO₂CH₂C₆H₄SO₂Me-4 4-Cl — 1-338 NHCO₂CH₂C₆H₄SO₂Me-3 4-Cl — 1-339 NHCO₂CH₂C₆H₄Ph-4 4-Cl — 1-340 NHCO₂CH₂C₆H₄Ph-3 4-Cl — 1-341 NHCO₂CH₂Py-2 4-Cl — 1-342 NHCO₂CH₂(6-Me-2-Py) 4-Cl — 1-343 NHCO₂C(CH₃)₂Py-4 4-Cl — 1-344 NHCO₂CH₂(2-thiazolyl) 4-Cl — 1-345 NHCO₂CH₂(2-benzthiazolyl) 4-Cl — 1-346 NHCO₂CH₂CH₂OMe 4-Cl — 1-347 NHCO₂CH₂CH₂OEt 4-Cl — 1-348 NHCO₂CH₂CH₂OPr-i 4-Cl — 1-349 NHCO₂CH₂CH₂OBu-i 4-Cl — 1-350 NHCO₂CH₂CH₂OCH₂CH₂OMe 4-Cl — 1-351 NHCO₂CH₂CH₂OC₆H₄Cl-4 4-Cl — 1-352 NHCOCH₂OPh 4-Cl — 1-353 NHCOCH₂OC₆H₄F-3 4-Cl — 1-354 NHCOCH₂OC₆H₄OCF₃-3 4-Cl — 1-355 NHCO₂CH₂CH₂OCH₂Ph 4-Cl — 1-356 NHCO₂(1,1-dimethyl-3- 4-Cl — phenyl-2-pentynyl) 1-357 NHCO₂CH₂CH₂OCH₂CH₂Ph 4-Cl — 1-358 NHCO₂(1,1-dimethyl-3- 4-Cl — phenyl-2-pentynyl) 1-359 NHCO₂(CH₂)₄SMe 4-Cl — 1-360 NHCO₂(CH₂)₄SCF₃ 4-Cl — 1-361 NHCO₂(CH₂)₄SPh 4-Cl — 1-362 NHCO₂(CH₂)₄SOMe 4-Cl — 1-363 NHCO₂(CH₂)₄SOCF₃ 4-Cl — 1-364 NHCO₂(CH₂)₄SOPh 4-Cl — 1-365 NHCO₂(CH₂)₄SO₂Me 4-Cl — 1-366 NHCO₂(CH₂)₄SO₂CF₃ 4-Cl — 1-367 NHCO₂(CH₂)₄SO₂Ph 4-Cl — 1-368 NHCO₂Ph 4-Cl — 1-369 NHCO₂C₆H₄OMe-4 4-Cl — 1-370 NHCONHMe 4-Cl — 1-371 NHCONHC₂H₅ 4-Cl — 1-372 NHCONHPr-n 4-Cl — 1-373 NHCONHBu-t 4-Cl — 1-374 NHCONHBu-s 4-Cl — 1-375 NHCONH(Hex-n) 4-Cl — 1-376 NHCOCH₂CF₃ — — 1-377 NHCOC₂F₅ — — 1-378 NHCOCH₂CH₂F — — 1-379 NHCOC(CH₃)₂CF₃ — — 1-380 NHCOCH₂CH₂CF₃ — — 107-109 1-381 NHCOCH₂C₂F₅ — — 1-382 NHCOCH₂CH═CH₂ — — 1-383 CHCOCH₂CH═CMe₂ — — 1-384 NHCOC(CH₃)₂CH═CH₂ — — 1-385 NHCOC(CH₃)₂CH═CHCH₃ — — 1-386 NHCOCH₂CH═CHCl — — 1-387 NHCOCH₂CH═CHCF₃ — — 1-388 NHCOCH₂CI═CI₂ — — 1-389 NHCO(1,1-dimethyl-2- — — propynyl) 1-390 NHCO(2-butynyl) — — 1-391 NHCO(1,1-dimethyl-2- — — butynyl) 1-392 NHCO(1,1-dimethyl-2- — — pentynyl) 1-393 NHCO(1-propynyl) — — 193-194 1-394 NHCO(1,1-dimethyl-3-Iodo- — — 2-pentynyl) 1-395 NHCO(4,4,4-trifluoro-2- — — butynyl) 1-396 NHCO(CH₂)₄CO₂H — — 127-129 1-397 NHCOCH₂CH₂CH₂NHMe₂ — — 1-398 NHCO(CH₂)₄NH₂ — — 1-399 NHCOCH₂NHCH₂Ph — — 1-400 NHCOCH₂N(CH₂Ph)(CO₂Bu-t) — — 1-401 NHCOCH₂CH₂NMe₂ — — 1-402 NHCOCH₂CH₂NHEt — — 1-403 NHCOCH₂CH₂NHPr-n — — 1-404 NHCOCH₂CH₂OC₆H₄Cl-4 — — 1-405 NHCOCH₂OPh — — 1-406 NHCOCH₂OC₆H₄F-3 — — 108-112 1-407 NHCOCH₂OC₆H₄OCF₃-3 — — 128-129 1-408 NHCOCH₂OC₆H₄CN-2 — — 198-200 1-409 NHCOCH₂OC₆H₄F-4 — — 86-87 1-410 NHCOCH₂OC₆H₃(3,4- — — 110-114 methylenedioxy) 1-411 NHCOCH₂OC₆H₄(CONH₂)-2 — — 1-412 NHCOCH₂OC₆H₃(3,4-(OCH₃)₂) — — 1-413 NHCOCH₂O(6-CF₃-pyrimidin- — — 4-yl) 1-414 NHCOCH₂O(3-Py) — — oil 1-415 NHCO₂CH₂CF₃ — — 1-416 NHCO₂C₂F₅ — — 1-417 NHCO₂CH₂CH₂F — — 1-418 NHCO₂C(CH₃)₂CF₃ — — 1-419 NHCO₂CH₂CH₂CF₃ — — 1-420 NHCO₂CH₂C₂F₅ — — 1-421 NHCO₂CH₂CH═CH₂ — — 1-422 NHCO₂CH₂CH═CMe₂ — — 1-423 NHCO₂C(CH₃)₂CH═CH₂ — — 1-424 NHCO₂C(CH₃)₂CH═CHCH₃ — — 1-425 NHCO₂CH₂CH═CHCl — — 1-426 NHCO₂CH₂CH═CHCF₃ — — 1-427 NHCO₂CH₂CI═CI₂ — — 1-428 NHCO₂(1,1-dimethyl-2- — — propynyl) 1-429 NHCO₂(2-butynyl) — — 37-39 1-430 NHCO₂(1,1-dimethyl-2- — — butynyl) 1-431 NHCO₂(1,1-dimethyl-2- — — pentynyl) 1-432 NHCO₂(1-propynyl) — — 1-433 NHCO₂(1,1-dimethyl-3-Iodo- — — 2-pentynyl) 1-434 NHCO₂(4,4,4-trifluoro-2- — — butynyl) 1-435 NHCO₂(1,1-dimethyl-3- — — phenyl-2-pentynyl) 1-436 NHCO₂CH₂CH₂NHCO₂Bu-t — — 115-117 1-437 NHCO₂CH₂CH₂NHCO₂Et — — 1-438 NHCO₂CH₂N(CH₂Ph)(CO₂Bu-t) — — 1-439 NHCO₂CH₂NCH₂Ph — — 1-440 NHCO₂CH₂CH₂NCH₂Ph — — 1-441 NHCO₂CH₂CH₂NCH₂C₆H₄Cl-4 — — 1-442 NHCO₂CH₂CH₂NHMe — — 1-443 NHCO₂CH₂C(CH₃)₂N(CH₃)₂ — — 1-444 NHCO₂CH(CH₃)CH₂N(CH₃)₂ — — 1-445 NHCO₂CH₂C₃H₅-c — — 1-446 NHCO₂CH(CH₃)C₃H₅-c — — 1-447 NHCO₂CH₂C₆H₁₁-c — — 44-47 1-448 NHCO₂CH(CH₃)CH₂Ph — — 1-449 NHCO₂CH(CH₃)Ph — — 1-450 NHCO₂C(CH₃)₂Ph — — 1-451 NHCO₂CH₂C₆H₄CF₃-4 — — 1-452 NHCO₂CH₂C₆H₄CN-4 — — 55-59 1-453 NHCO₂CH₂C₆H₄CN-3 — — 45-48 1-454 NHCO₂CH₂C₆H₄Cl-4 — — 47-49 1-455 NHCO₂CH₂C₆H₄Cl-3 — — 39-44 1-456 NHCO₂CH₂C₆H₄OMe-3 — — 1-457 NHCO₂CH₂C₆H₄OMe-2 — — 1-458 NHCO₂CH₂C₆H₄Me-4 — — 40-45 1-459 NHCO₂CH₂C₆H₄Me-3 — — 46-49 1-460 NHCO₂CH₂C₆H₄Me-2 — — 57-60 1-461 NHCO₂CH₂C₆H₄SO₂Me-4 — — 66-70 1-462 NHCO₂CH₂C₆H₄SO₂Me-3 — — 45-50 1-463 NHCO₂CH₂C₆H₄Ph-4 — — 60-64 1-464 NHCO₂CH₂C₆H₄Ph-3 — — 59-63 1-465 NHCO₂CH₂C₆H₄OCH₃-4 — — 1-466 NHCO₂CH₂C₆H₃(3,4- — — methylenedioxy) 1-467 NHCO₂CH₂Py-2 — — 1-468 NHCO₂CH₂(6-Me-2-Py) — — 94-96 1-469 NHCO₂C(CH₃)₂Py-4 — — 168-169 1-470 NHCO₂CH₂(2-thiazolyl) — — 1-471 NHCO₂CH₂(2-benzthiazolyl) — — 1-472 NHCO₂CH₂(3-Py) — — 140-141 1-473 NHCO₂CH₂(4-Py) — — 52-55 1-474 NHCO₂CH(CH₃)(4-Py) — — 1-475 NHCO₂CH₂CH₂OMe — — 81-82 1-476 NHCO₂CH₂CH₂OEt — — 89-91 1-477 NHCO₂CH₂CH₂OPr-i — — 1-478 NHCO₂CH₂CH₂OBu-i — — 93-94 1-479 NHCO₂CH₂CH₂OCH₂CH₂OMe — — 115-117 1-480 NHCO₂C(CH₃)₂CH₂OCH₃ — — 1-481 NHCO₂CH(CH₃)CH₂OCH₃ — — 1-482 NHCO₂CH₂CH₂OC₆H₄Cl-4 — — 1-483 NHCO₂CH₂OPh — — 1-484 NHCO₂CH₂OC₆H₄F-3 — — 1-485 NHCO₂CH₂OC₆H₄OCF₃-3 — — 1-486 NHCO₂CH₂CH₂OCH₂Ph — — 1-487 NHCO₂CH₂CH₂OCH₂CH₂Ph — — 1-488 NHCO₂(CH₂)₄SMe — — 1-489 NHCO₂(CH₂)₄SCF₃ — — 1-490 NHCO₂(CH₂)₄SPh — — 1-491 NHCO₂(CH₂)₄SOMe — — 1-492 NHCO₂(CH₂)₄SOCF₃ — — 1-493 NHCO₂(CH₂)₄SOPh — — 1-494 NHCO₂(CH₂)₄SO₂Me — — 123-124 1-495 NHCO₂(CH₂)₄SO₂CF₃ — — 1-496 NHCO₂(CH₂)₄SO₂Ph — — 1-497 NHCO₂Ph — — 129-131 1-498 NHCO₂C₆H₄OMe-4 — — 179-181 1-499 NHCOCH₂CH₂CH₂COCH₃ — —

TABLE 2

mp No Z¹¹ R¹¹ (X)_(n1) ° C. 2-1 H Me — 2-2 NH₂ Me — 2-3 NH₂ Bu-t — 2-4 NH₂ OC₂H₅ — 2-5 NH₂ OCH₃ — 2-6 NH₂ C₂H₅ — 2-7 NHCHO Me — 2-8 NHCOCH₃ Me — 2-9 NHCOC₂H₅ Me — 2-10 NHCOPr-n Me — 2-11 NHCOPr-i Me — 2-12 NHCOBu-n Me — 2-13 NHCOBu-i Me — 2-14 NHCOBu-s Me — 2-15 NHCOBu-t Me — 2-16 NHCOBu-t OMe — 2-17 NHCOCH₂CF₃ Me — 2-18 NHCOC₂F₅ Me — 2-19 NHCOCH₂CH₂F Me — 2-20 NHCOC(CH₃)₂CF₃ Me — 2-21 NHCOCH₂CH₂CF₃ Me — 2-22 NHCOCH₂C₂F₅ Me — 2-23 NHCOCH₂CH═CH₂ Me — 2-24 NHCOCH₂CH═CMe₂ Me — 2-25 NHCOC(CH₃)₂CH═CH₂ Me — 2-26 NHCOC(CH₃)₂CH═CHCH₃ Me — 2-27 NHCOCH₂CH═CHCl Me — 2-28 NHCOCH₂CH═CHCF₃ Me — 2-29 NHCOCH₂CI═CI₂ Me — 2-30 NHCO(1,1-dimethyl-2- Me — propynyl) 2-31 NHCO(2-butynyl) Me — 2-32 NHCO(1,1-dimethyl-2- Me — butynyl) 2-33 NHCO(1,1-dimethyl-2- Me — pentynyl) 2-34 NHCO(1-propynyl) Me — 2-35 NHCO(1,1-dimethyl-3-Iodo- Me — 2-pentynyl) 2-36 NHCO(4,4,4-trifluoro-2- Me — butynyl) 2-37 NHCOPr-c Me — 2-38 NHCOHex-c Me — 2-39 NHCO(CH₂)₄CO₂H Me — 2-40 NHCOCH₂CH₂NHCO₂Bu-t Me — 2-41 NHCOCH₂CH₂NHCO₂Et Me — 2-42 NHCOCH₂CH₂CH₂NHCOCH₃ Me — 2-43 NHCOCH₂CH₂CH₂NHMe₂ Me — 2-44 NHCOCH₂CH₂N(Me)COCH₃ Me — 2-45 NHCOCH₂CH₂NHCOPh Me — 2-46 NHCOCH₂CH₂N(Me)COPh Me — 2-47 NHCOCH₂CH₂NHPh Me — 2-48 NHCO(CH₂)₄NH₂ Me — 2-49 NHCOCH₂NHCH₂Ph Me — 2-50 NHCOCH₂N(CH₂Ph)(CO₂Bu-t) Me — 2-51 NHCOCH₂CH₂OC₆H₄Cl-4 Me — 2-52 NHCOCH₂OPh Me — 2-53 NHCOCH₂OC₆H₄F-3 Me — 2-54 NHCOCH₂OC₆H₄OCF₃-3 Me — 2-55 NHCO(CH₂)₄SMe Me — 2-56 NHCOCH₂CH₂OEt Me — 2-57 NHCOCH₂CH₂OPr-i Me — 2-58 NHCOCH₂CH₂OBu-i Me — 2-59 NHCOCH₂CH₂OCH₂CH₂OMe Me — 2-60 NHCO₂CH₃ Me — 2-61 NHCO₂C₂H₅ Me — 2-62 NHCO₂Pr-n Me — 2-63 NHCO₂Pr-i Me — 2-64 NHCO₂Bu-n Me — 2-65 NHCO₂Bu-i Me — 2-66 NHCO₂Bu-s Me — 2-67 NHCO₂Bu-t i-Pr — 2-68 NHCO₂Bu-t Me — 2-69 NHCO₂Bu-t t-Bu — 2-70 NHCO₂Bu-t Et — 2-71 NHCO₂Bu-t CH═CH2 — 2-72 NHCO₂Bu-t OMe — 2-73 NHCO₂Bu-t OEt — 2-74 NHCO₂Bu-t OCH₂CH₂OEt — 2-75 NHCO₂Bu-t OPr-i — 2-76 NHCO₂Bu-t OBu-n — 2-77 NHCO₂Bu-t SMe — 2-78 NHCO₂Bu-t SOMe — 2-79 NHCO₂Bu-t SO₂Me — 2-80 NHCO₂Bu-t NMe₂ — 2-81 NHCO₂Bu-t N(Me)(CO₂Bu-t) — 2-82 NHCO₂Bu-t CN — 2-83 NHCO₂Bu-t morphorino — 2-84 NHCO₂Bu-t Ph — 2-85 NHCO₂Bu-t CO₂C₂H₅ — 2-86 NHCO₂Bu-t CONHCH₃ — 2-87 NHCO₂Bu-t CF₃ — 2-88 NHCO₂Bu-t OH — 2-89 NHCO₂Bu-t SH — 2-90 NHCO₂Bu-t CH₂CI═CI₂ — 2-91 NHCO₂Bu-t etynyl — 2-92 NHCO₂Bu-t propargyl — 2-93 NHCO₂Bu-t (3-iodo-2- — propynyl) 2-94 NHCO₂Bu-t Ph — 2-95 NHCO₂Bu-t C₆H₄OMe-4 — 2-96 NHCO₂Bu-t 2-pyridyl — 2-97 NHCO₂Bu-t 4-CF₃-2-oxazolyl — 2-98 NHCO₂Bu-t 3-CF₃-5-Cl-2- — pyridyl 2-99 NHCO₂Bu-t pyrrolidino — 2-100 NHCO₂Bu-t COMe — 2-101 NHCO₂Bu-t CONHMe — 2-102 NHCO₂Bu-t CONMe₂ — 2-103 NHCO₂Bu-t COPr-c — 2-104 NHCO₂Bu-t COPh — 2-105 NHCO₂Bu-t COCH₂CH═CH₂ — 2-106 NHCO₂Bu-t CO(propargyl) — 2-107 NHCO₂Bu-t CO₂Me — 2-108 NHCO₂Bu-t CO₂Ph — 2-109 NHCO₂Bu-t CO₂CH₂CH═CH₂ — 2-110 NHCO₂Bu-t CO₂(propargyl) — 2-111 NHCO₂Bu-t Me 2-Cl 2-112 NHCO₂Bu-t Me 3-Cl 2-113 NHCO₂Bu-t Me 4-Cl 2-114 NHCO₂Bu-t Me 2,4-Cl₂ 2-115 NHCO₂Bu-t Me 3,5-Cl₂ 2-116 NHCO₂Bu-t Me 3,4,5-Cl₃ 2-117 NHCO₂Bu-t Me 2-Me 2-118 NHCO₂Bu-n NH₂ — 2-119 NHCO₂Bu-n NHCO₂Bu-t — 2-120 NHCO₂CH₂CF₃ Me — 2-121 NHCO₂C₂F₅ Me — 2-122 NHCO₂CH₂CH₂F Me — 2-123 NHCO₂C(CH₃)₂CF₃ Me — 2-124 NHCO₂CH₂CH₂CF₃ Me — 2-125 NHCO₂CH₂C₂F₅ Me — 2-126 NHCO₂CH₂CH═CH₂ Me — 2-127 NHCO₂CH₂CH═CMe₂ Me — 2-128 NHCO₂C(CH₃)₂CH═CH₂ Me — 2-129 NHCO₂C(CH₃)₂CH═CHCH₃ Me — 2-130 NHCO₂CH₂CH═CHCl Me — 2-131 NHCO₂CH₂CH═CHCF₃ Me — 2-132 NHCO₂CH₂CI═CI₂ Me — 2-133 NHCO₂(1,1-dimethyl-2- Me — propynyl) 2-134 NHCO₂(2-butynyl) Me — 2-135 NBCO₂(1,1-dimethyl-2- Me — butynyl) 2-136 NHCO₂(1,1-dimethyl-2- Me — pentynyl) 2-137 NHCO₂(1-propynyl) Me — 2-138 NHCO₂(1,1-dimethyl-3-Iodo- Me — 2-pentynyl) 2-139 NHCO₂(4,4,4-trifluoro-2- Me — butynyl) 2-140 NHCO₂Pr-c Me — 2-141 NHCO₂Hex-c Me — 2-142 NHCO₂CH₂CH₂NHCO₂Bu-t Me — 2-143 NHCO₂CH₂CH₂NHCO₂Et Me — 2-144 NHCO₂CH₂CH₂CH₂NHCOCH₃ Me — 2-145 NHCO₂CH₂CH₂CH₂NHMe₂ Me — 2-146 NHCO₂CH₂CH₂N(Me)COCH₃ Me — 2-147 NHCO₂CH₂CH₂NHCOPh Me — 2-148 NHCO₂CH₂CH₂N(Me)COPh Me — 2-149 NHCO₂CH₂CH₂NHPh Me — 2-150 NHCO₂(CH₂)₄NH₂ Me — 2-151 NHCO₂CH₂NHCH₂Ph Me — 2-152 NHCO₂CH₂N(CH₂Ph)(CO₂Bu-t) Me — 2-153 NHCO₂CH₂C₃H₅-c Me — 2-154 NHCO₂CH(CH₃)C₃H₅-c Me — 2-155 NHCO₂CH₂C₆H₁₁-c Me — 2-156 NHCO₂CH₂Ph Me — 2-157 NHCO₂CH(CH₃)CH₂Ph Me — 2-158 NHCO₂CH(CH₃)Ph Me — 2-159 NHCO₂C(CH₃)₂Ph Me — 2-160 NHCO₂CH₂C₆H₄CF₃-4 Me — 2-161 NHCO₂CH₂C₆H₄CN-4 Me — 2-162 NHCO₂CH₂C₆H₄CN-3 Me — 2-163 NHCO₂CH₂C₆H₄Cl-4 Me — 2-164 NHCO₂CH₂C₆H₄Cl-3 Me — 2-165 NHCO₂CH₂C₆H₄OMe-3 Me — 2-166 NHCO₂CH₂C₆H₄OMe-2 Me — 2-167 NHCO₂CH₂C₆H₄Me-4 Me — 2-168 NHCO₂CH₂C₆H₄Me-3 Me — 2-169 NHCO₂CH₂C₆H₄Me-2 Me — 2-170 NHCO₂CH₂C₆H₄SO₂Me-4 Me — 2-171 NHCO₂CH₂C₆H₄SO₂Me-3 Me — 2-172 NHCO₂CH₂C₆H₄Ph-4 Me — 2-173 NHCO₂CH₂C₆H₄Ph-3 Me — 2-174 NHCO₂CH₂Py-2 Me — 2-175 NHCO₂CH₂(6-Me-2-Py) Me — 2-176 NHCO₂C(CH₃)₂Py-4 Me — 2-177 NHCO₂CH₂(2-thiazolyl) Me — 2-178 NHCO₂CH₂(2-benzthiazolyl) Me — 2-179 NHCO₂CH₂CH₂OMe Me — 2-180 NHCO₂CH₂CH₂OEt Me — 2-181 NHCO₂CH₂CH₂OPr-i Me — 2-182 NHCO₂CH₂CH₂OBu-i Me — 2-183 NHCO₂CH₂CH₂OCH₂CH₂OMe Me — 2-184 NHCO₂CH₂CH₂OEt i-Pr — 2-185 NHCO₂CH₂CH₂OC₆H₄Cl-4 Me — 2-186 NHCOCH₂OPh Me — 2-187 NHCOCH₂OC₆H₄F-3 Me — 2-188 NHCOCH₂OC₆H₄OCF₃-3 Me — 2-189 NHCO₂CH₂CH₂OCH₂Ph Me — 2-190 NHCO₂CH₂CH₂OCH₂CH₂Ph Me — 2-191 NHCO₂(1,1-dimethyl-3- Me — phenyl-2-pentynyl) 2-192 NHCO₂(CH₂)₄SMe Me — 2-193 NHCO₂(CH₂)₄SCF₃ Me — 2-194 NHCO₂(CH₂)₄SPh Me — 2-195 NHCO₂(CH₂)₄SOMe Me — 2-196 NHCO₂(CH₂)₄SOCF₃ Me — 2-197 NHCO₂(CH₂)₄SOPh Me — 2-198 NHCO₂(CH₂)₄SO₂Me Me — 2-199 NHCO₂(CH₂)₄SO₂CF₃ Me — 2-200 NHCO₂(CH₂)₄SO₂Ph Me — 2-201 NHCO₂Ph Me — 2-202 NHCO₂C₆H₄OMe-4 Me — 2-203 NHCONHMe Me — 2-204 NHCONHC₂H₅ Me — 2-205 NHCONHPr-n Me — 2-206 NHCONHBu-t Me — 2-207 NHCONHBu-s Me — 2-208 NHCONH(Hex-n) Me — 2-209 H Cl — 2-210 NH₂ Cl — 2-211 NHCHO Cl — 2-212 NHCOCH₂CF₃ Cl — 2-213 NHCOC₂F₅ Cl — 2-214 NHCOCH₂CH₂F Cl — 2-215 NHCOC(CH₃)₂CF₃ Cl — 2-216 NHCOCH₂CH₂CF₃ Cl — 2-217 NHCOCH₂C₂F₅ Cl — 2-218 NHCOCH₂CH═CH₂ Cl — 2-219 NHCOCH₂CH═CMe₂ Cl — 2-220 NHCOC(CH₃)₂CH═CH₂ Cl — 2-221 NHCOC(CH₃)₂CH═CHCH₃ Cl — 2-222 NHCOCH₂CH═CHCl Cl — 2-223 NHCOCH₂CH═CHCF₃ Cl — 2-224 NHCOCH₂CI═CI₂ Cl — 2-225 NHCO(1,1-dimethyl-2- Cl — propynyl) 2-226 NHCO(2-butynyl) Cl — 2-227 NHCO(1,1-dimethyl-2- Cl — butynyl) 2-228 NHCO(1,1-dimethyl-2- Cl — pentynyl) 2-229 NHCO(1-propynyl) Cl — 2-230 NHCO(1,1-dimethyl-3-Iodo- Cl — 2-pentynyl) 2-231 NHCO(4,4,4-trifluoro-2- Cl — butynyl) 2-232 NHCOPr-c Cl — 2-233 NHCOHex-c Cl — 2-234 NHCO(CH₂)₄CO₂H Cl — 2-235 NHCOCH₂CH₂NHCO₂Bu-t Cl — 2-236 NHCOCH₂CH₂NHCO₂Et Cl — 2-237 NHCOCH₂CH₂CH₂NHCOCH₃ Cl — 2-238 NHCOCH₂CH₂CH₂NHMe₂ Cl — 2-239 NHCOCH₂CH₂N(Me)COCH₃ Cl — 2-240 NHCOCH₂CH₂NHCOPh Cl — 2-241 NHCOCH₂CH₂N(Me)COPh Cl — 2-242 NHCOCH₂CH₂NHPh Cl — 2-243 NHCO(CH₂)₄NH₂ Cl — 2-244 NHCOCH₂NHCH₂Ph Cl — 2-245 NHCOCH₂N(CH₂Ph)(CO₂Bu-t) Cl — 2-246 NHCOCH₂CH₂OC₆H₄Cl-4 Cl — 2-247 NHCOCH₂OPh Cl — 2-248 NHCOCH₂OC₆H₄F-3 Cl — 2-249 NHCOCH₂OC₆H₄OCF₃-3 Cl — 2-250 NHCO(CH₂)₄SMe Cl — 2-251 NHCOCH₂CH₂OEt Cl — 2-252 NHCOCH₂CH₂OPr-i Cl — 2-253 NHCOCH₂CH₂OBu-i Cl — 2-254 NHCOCH₂CH₂OCH₂CH₂OMe Cl — 2-255 NHCO₂CH₃ Cl — 2-256 NHCO₂C₂H₅ Cl — 2-257 NHCO₂Pr-n Cl — 2-258 NHCO₂Pr-i Cl — 2-259 NHCO₂Bu-n Cl — 2-260 NHCO₂Bu-i Cl — 2-261 NHCO₂Bu-s Cl — 2-262 NHCO₂Bu-t Cl — 2-263 NHCO₂Bu-t Br — 91-93 2-264 NHCO₂Bu-t Cl 2-Cl 2-265 NHCO₂Bu-t Cl 3-Cl 2-266 NHCO₂Bu-t Cl 4-Cl 2-267 NHCO₂Bu-t Cl 2,4-Cl₂ 2-268 NHCO₂Bu-t Cl 3,5-Cl₂ 2-269 NHCO₂Bu-t Cl 3,4,5-Cl₃ 2-270 NHCO₂Bu-t Cl 2-Me 2-271 NHCO₂CH₂CF₃ Cl — 2-272 NHCO₂C₂F₅ Cl — 2-273 NHCO₂CH₂CH₂F Cl — 2-274 NHCO₂C(CH₃)₂CF₃ Cl — 2-275 NHCO₂CH₂CH₂CF₃ Cl — 2-276 NHCO₂CH₂C₂F₅ Cl — 2-277 NHCO₂CH₂CH═CH₂ Cl — 2-278 NHCO₂CH₂CH═CMe₂ Cl — 2-279 NHCO₂C(CH₃)₂CH═CH₂ Cl — 2-280 NHCO₂C(CH₃)₂CH═CHCH₃ Cl — 2-281 NHCO₂CH₂CH═CHCl Cl — 2-282 NHCO₂CH₂CH═CHCF₃ Cl — 2-283 NHCO₂CH₂CI═CI₂ Cl — 2-284 NHCO₂(1,1-dimethyl-2- Cl — propynyl) 2-285 NHCO₂(2-butynyl) Cl — 2-286 NHCO₂(1,1-dimethyl-2- Cl — butynyl) 2-287 NHCO₂(1,1-dimethyl-2- Cl — pentynyl) 2-288 NHCO₂(1-propynyl) Cl — 2-289 NHCO₂(1,1-dimethyl-3-Iodo- Cl — 2-pentynyl) 2-290 NHCO₂(4,4,4-trifluoro-2- Cl — butynyl) 2-291 NHCO₂Pr-c Cl — 2-292 NHCO₂Hex-c Cl — 2-293 NHCO₂CH₂CH₂NHCO₂Bu-t Cl — 2-294 NHCO₂CH₂CH₂NHCO₂Et Cl — 2-295 NHCO₂CH₂CH₂CH₂NHCOCH₃ Cl — 2-296 NHCO₂CH₂CH₂CH₂NMe₂ Cl — 2-297 NHCO₂CH₂CH₂N(Me)COCH₃ Cl — 2-298 NHCO₂CH₂CH₂NHCOPh Cl — 2-299 NHCO₂CH₂CH₂N(Me)COPh Cl — 2-300 NHCO₂CH₂CH₂NHPh Cl — 2-301 NHCO₂(CH₂)₄NH₂ Cl — 2-302 NHCO₂CH₂NHCH₂Ph Cl — 2-303 NHCO₂CH₂N(CH₂Ph)(CO₂Bu-t) Cl — 2-304 NHCO₂CH₂C₃H₅-c Cl — 2-305 NHCO₂CH(CH₃)C₃H₅-c Cl — 2-306 NHCO₂CH₂C₆H₁₁-c Cl — 2-307 NHCO₂CH₂Ph Cl — 2-308 NHCO₂CH(CH₃)CH₂Ph Cl — 2-309 NHCO₂CH(CH₃)Ph Cl — 2-310 NHCO₂C(CH₃)₂Ph Cl — 2-311 NHCO₂CH₂C₆H₄CF₃-4 Cl — 2-312 NHCO₂CH₂C₆H₄CN-4 Cl — 2-313 NHCO₂CH₂C₆H₄CN-3 Cl — 2-314 NHCO₂CH₂C₆H₄Cl-4 Cl — 2-315 NHCO₂CH₂C₆H₄Cl-3 Cl — 2-316 NHCO₂CH₂C₆H₄OMe-3 Cl — 2-317 NHCO₂CH₂C₆H₄OMe-2 Cl — 2-318 NHCO₂CH₂C₆H₄Me-4 Cl — 2-319 NHCO₂CH₂C₆H₄Me-3 Cl — 2-320 NHCO₂CH₂C₆H₄Me-2 Cl — 2-321 NHCO₂CH₂C₆H₄SO₂Me-4 Cl — 2-322 NHCO₂CH₂C₆H₄SO₂Me-3 Cl — 2-323 NHCO₂CH₂C₆H₄Ph-4 Cl — 2-324 NHCO₂CH₂C₆H₄Ph-3 Cl — 2-325 NHCO₂CH₂Py-2 Cl — 2-326 NHCO₂CH₂(6-Me-2-Py) Cl — 2-327 NHCO₂C(CH₃)₂Py-4 Cl — 2-328 NHCO₂CH₂(2-thiazolyl) Cl — 2-329 NHCO₂CH₂(2-benzthiazolyl) Cl — 2-330 NHCO₂CH₂CH₂OMe Cl — 2-331 NHCO₂CH₂CH₂OEt Cl — 2-332 NHCO₂CH₂CH₂OPr-i Cl — 2-333 NHCO₂CH₂CH₂OBu-i Cl — 2-334 NHCO₂CH₂CH₂OCH₂CH₂OMe Cl — 2-335 NHCO₂CH₂CH₂OC₆H₄Cl-4 Cl — 2-336 NHCOCH₂OPh Cl — 2-337 NHCOCH₂OC₆H₄F-3 Cl — 2-338 NHCOCH₂OC₆H₄OCF₃-3 Cl — 2-339 NHCO₂CH₂CH₂OCH₂Ph Cl — 2-340 NHCO₂(1,1-dimethyl-3- Cl — phenyl-2-pentynyl) 2-341 NHCO₂CH₂CH₂OCH₂CH₂Ph Cl — 2-342 NHCO₂(1,1-dimethyl-3- Cl — phenyl-2-pentynyl) 2-343 NHCO₂(CH₂)₄SMe Cl — 2-344 NHCO₂(CH₂)₄SCF₃ Cl — 2-345 NHCO₂(CH₂)₄SPh Cl — 2-346 NHCO₂(CH₂)₄SOMe Cl — 2-347 NHCO₂(CH₂)₄SOCF₃ Cl — 2-348 NHCO₂(CH₂)₄SOPh Cl — 2-349 NHCO₂(CH₂)₄SO₂Me Cl — 2-350 NHCO₂(CH₂)₄SO₂CF₃ Cl — 2-351 NHCO₂(CH₂)₄SO₂Ph Cl — 2-352 NHCO₂Ph Cl — 2-353 NHCO₂C₆H₄OMe-4 Cl — 2-354 NHCONHMe Cl — 2-355 NHCONHC₂H₅ Cl — 2-356 NHCONHPr-n Cl — 2-357 NHCONHBu-t Cl — 2-358 NHCONHBu-s Cl — 2-359 NHCONH(Hex-n) Cl — 2-360 NHCOCH₂CF₃ — — 2-361 NHCOC₂F₅ — — 2-362 NHCOCH₂CH₂F — — 2-363 NHCOC(CH₃)₂CF₃ — — 2-364 NHCOCH₂CH₂CF₃ — — 2-365 NHCOCH₂C₂F₅ — — 2-366 NHCOCH₂CH═CH₂ — — 2-367 NHCOCH₂CH═CMe₂ — — 2-368 NHCOC(CH₃)₂CH═CH₂ — — 2-369 NHCOC(CH₃)₂CH═CHCH₃ — — 2-370 NHCOCH₂CH═CHCl — — 2-371 NHCOCH₂CH═CHCF₃ — — 2-372 NHCOCH₂CI═CI₂ — — 2-373 NHCO(1,1-dimethyl-2- — — propynyl) 2-374 NHCO(2-butynyl) — — 2-375 NHCO(1,1-dimethyl-2- — — butynyl) 2-376 NHCO(1,1,dimethyl-2- — — pentynyl) 2-377 NHCO(1-propynyl) — — 2-378 NHCO(1,1-dimethyl-3-Iodo- — — 2-pentynyl) 2-379 NHCO(4,4,4-trifluoro-2- — — butynyl) 2-380 NHCO(CH₂)₄CO₂H — — 2-381 NHCOCH₂CH₂CH₂NHMe₂ — — 2-382 NHCO(CH₂)₄NH₂ — — 2-383 NHCOCH₂NHCH₂Ph — — 2-384 NHCOCH₂N(CH₂Ph)(CO₂Bu-t) — — 2-385 NHCOCH₂CH₂NMe₂ — — 2-386 NHCOCH₂CH₂NHEt — — 2-387 NHCOCH₂CH₂NHPr-n — — 2-388 NHCOCH₂CH₂OC₆H₄Cl-4 — — 2-389 NHCOCH₂OPh — — 95-97 2-390 NHCOCH₂OC₆H₄F-3 — — 2-391 NHCOCH₂OC₆H₄OCF₃-3 — — 112-113 2-392 NHCOCH₂OC₆H₄CN-2 — — 159-162 2-393 NHCOCH₂OC₆H₄F-4 — — 2-394 NHCOCH₂OC₆H₃(3,4- — — 67-72 methylenedioxy) 2-395 NHCOCH₂OC₆H₄(CONH₂)-2 — — 2-396 NHCOCH₂OC₆H₃(3,4-(OCH₃)₂) — — 140-141 2-397 NHCOCH₂O(6-CF₃-pyrimidin- — — 108-111 4-y1) (dec.) 2-398 NHCOCH₂O (3-Py) — — 2-399 NHCOCH₂CH₂CH₂COCH₃ — — 2-400 NHCO₂CH₂CF₃ — — 2-401 NHCO₂C₂F₅ — — 2-402 NHCO₂CH₂CH₂F — — 2-403 NHCO₂C(CH₃)₂CF₃ — — 2-404 NHCO₂CH₂CH₂CF₃ — — 2-405 NHCO₂CH₂C₂F₅ — — 2-406 NHCO₂CH₂CH═CH₂ — — 2-407 NHCO₂CH₂CH═CMe₂ — — 2-408 NHCO₂C(CH₃)₂CH═CH₂ — — 2-409 NHCO₂C(CH₃)₂CH═CHCH₃ — — 2-410 NHCO₂CH₂CH═CHCl — — 2-411 NHCO₂CH₂CH═CHCF₃ — — 2-412 NHCO₂CH₂CI═CI₂ — — 2-413 NHCO₂(1,1-dimethyl-2- — — propynyl) 2-414 NHCO₂(2-butynyl) — — 2-415 NHCO₂(1,1-dimethyl-2- — — butynyl) 2-416 NHCO₂(1,1-dimethyl-2- — — pentynyl) 2-417 NHCO₂(1-propynyl) — — 2-418 NHCO₂(1,1-dimethyl-3-Iodo- — — 2-pentynyl) 2-419 NHCO₂(4,4,4-trifluoro-2- — — butynyl) 2-420 NHCO₂(1,1-dimethyl-3- — — phenyl-2-pentynyl) 2-421 NHCO₂CH₂CH₂NHCO₂Bu-t — — 2-422 NHCO₂CH₂CH₂NHCO₂Et — — 2-423 NHCO₂CH₂N(CH₂Ph)(CO₂Bu-t) — — 2-424 NHCO₂CH₂NCH₂Ph — — 2-425 NHCO₂CH₂CH₂NCH₂Ph — — 2-426 NHCO₂CH₂CH₂NCH₂C₆H₄Cl-4 — — 2-427 NHCO₂CH₂CH₂NHMe — — 2-428 NHCO₂CH₂C(CH₃)₂N(CH₃)₂ — — 2-429 NHCO₂CH(CH₃)CH₂N(CH₃)₂ — — 2-430 NHCO₂CH₂C₃H₅-c — — 2-431 NHCO₂CH(CH₃)C₃H₅-c — — 2-432 NHCO₂CH₂C₆H₁₁-c — — 2-433 NHCO₂CH(CH₃)CH₂Ph — — 2-434 NHCO₂CH(CH₃)Ph — — 2-435 NHCO₂C(CH₃)₂Ph — — 2-436 NHCO₂CH₂C₆H₄CF₃-4 — — 2-437 NHCO₂CH₂C₆H₄CN-4 — — 2-438 NHCO₂CH₂C₆H₄CN-3 — — 2-439 NHCO₂CH₂C₆H₄Cl-4 — — 2-440 NHCO₂CH₂C₆H₄Cl-3 — — 2-441 NHCO₂CH₂C₆H₄OMe-3 — — 2-442 NHCO₂CH₂C₆H₄OMe-2 — — 2-443 NHCO₂CH₂C₆H₄Me-4 — — 2-444 NHCO₂CH₂C₆H₄Me-3 — — 2-445 NHCO₂CH₂C₆H₄Me-2 — — 2-446 NHCO₂CH₂C₆H₄SO₂Me-4 — — 2-447 NHCO₂CH₂C₆H₄SO₂Me-3 — — 2-448 NHCO₂CH₂C₆H₄Ph-4 — — 2-449 NHCO₂CH₂C₆H₄Ph-3 — — 2-450 NHCO₂CH₂C₆H₄OCH₃-4 — — 2-451 NHCO₂CH₂C₆H₃(3,4- — — methylenedioxy) 2-452 NHCO₂CH₂Py-2 — — 2-453 NHCO₂CH₂(6-Me-2-Py) — — 2-454 NHCO₂C(CH₃)₂Py-4 — — 2-455 NHCO₂CH₂(2-thiazolyl) — — 2-456 NHCO₂CH₂(2-benzthiazolyl) — — 2-457 NHCO₂CH₂(3-Py) — — 2-458 NHCO₂CH₂(4-Py) — — 2-459 NHCO₂CH(CH₃)(4-Py) — — 2-460 NHCO₂CH₂CH₂OMe — — 2-461 NHCO₂CH₂CH₂OEt — — 2-462 NHCO₂CH₂CH₂OPr-i — — 2-463 NHCO₂CH₂CH₂OBu-i — — 2-464 NHCO₂CH₂CH₂OCH₂CH₂OMe — — 2-465 NHCO₂C(CH₃)₂CH₂OCH₃ — — 2-466 NHCO₂CH(CH₃)CH₂OCH₃ — — 2-467 NHCO₂CH₂CH₂OC₆H₄Cl-4 — — 2-468 NHCO₂CH₂OPh — — 2-469 NHCO₂CH₂OC₆H₄F-3 — — 2-470 NHCO₂CH₂OC₆H₄OCF₃-3 — — 2-471 NHCO₂CH₂CH₂OCH₂Ph — — 2-472 NHCO₂CH₂CH₂OCH₂CH₂Ph — — 2-473 NHCO₂(CH₂)₄SMe — — 2-474 NHCO₂(CH₂)₄SCF₃ — — 2-475 NHCO₂(CH₂)₄SPh — — 2-476 NHCO₂(CH₂)₄SOMe — — 2-477 NHCO₂(CH₂)₄SOCF₃ — — 2-478 NHCO₂(CH₂)₄SOPh — — 2-479 NHCO₂(CH₂)₄SO₂Me — — 2-480 NHCO₂(CH₂)₄SO₂CF₃ — — 2-481 NHCO₂(CH₂)₄SO₂Ph — — 2-482 NHCO₂Ph — — 2-483 NHCO₂C₆H₄OMe-4 — —

TABLE 3

mp No Z R_(n2) (X)_(n1) ° C. 3-1 H 4-Me — 3-2 NH₂ 4-Me — 3-3 NH₂ 4-Bu-t — 3-4 NH₂ 4-OC₂H₅ — 3-5 NH₂ 5-CH₃ — 3-6 NH₂ 4-OCH₃ — 3-7 NH₂ 4-C₂H₅ — 3-8 NHCHO 4-Me — 3-9 NHCOCH₃ 4-Me — 3-10 NHCOC₂H₅ 4-Me — 3-11 NHCOPr-n 4-Me — 3-12 NHCOPr-i 4-Me — 3-13 NHCOBu-n 4-Me — 3-14 NHCOBu-i 4-Me — 3-15 NHCOBu-s 4-Me — 3-16 NHCOBu-t 4-Me — 3-17 NHCOBu-t 4-OMe — 3-18 NHCOCH₂CF₃ 4-Me — 3-19 NHCOC₂F₅ 4-Me — 3-20 NHCOCH₂CH₂F 4-Me — 3-21 NHCOC(CH₃)₂CF₃ 4-Me — 3-22 NHCOCH₂CH₂CF₃ 4-Me — 3-23 NHCOCH₂C₂F₅ 4-Me — 3-24 NHCOCH₂CH═CH₂ 4-Me — 3-25 NHCOCH₂CH═CMe₂ 4-Me — 3-26 NHCOC(CH₃)₂CH═CH₂ 4-Me — 3-27 NHCOC(CH₃)₂CH═CHCH₃ 4-Me — 3-28 NHCOCH₂CH═CHCl 4-Me — 3-29 NHCOCH₂CH═CHCF₃ 4-Me — 3-30 NHCOCH₂CI═CI₂ 4-Me — 3-31 NHCO(1,1-dimethyl-2- 4-Me — propynyl) 3-32 NHCO(2-butynyl) 4-Me — 3-33 NHCO(1,1-dimethyl-2- 4-Me — butynyl) 3-34 NHCO(1,1-dimethyl-2- 4-Me — pentynyl) 3-35 NHCO(1-propynyl) 4-Me — 3-36 NHCO(1,1-dimethyl-3-Iodo- 4-Me — 2-pentynyl) 3-37 NHCO(4,4,4-trifluoro-2- 4-Me — butynyl) 3-38 NHCOPr-c 4-Me — 3-39 NHCOHex-c 4-Me — 3-40 NHCO(CH₂)₄CO₂H 4-Me — 3-41 NHCOCH₂CH₂NHCO₂Bu-t 4-Me — 3-42 NHCOCH₂CH₂NHCO₂Et 4-Me — 3-43 NHCOCH₂CH₂CH₂NHCOCH₃ 4-Me — 3-44 NHCOCH₂CH₂CH₂NHMe₂ 4-Me — 3-45 NHCOCH₂CH₂N(Me)COCH₃ 4-Me — 3-46 NHCOCH₂CH₂NHCOPh 4-Me — 3-47 NHCOCH₂CH₂N(Me)COPh 4-Me — 3-48 NHCOCH₂CH₂NHPh 4-Me — 3-49 NHCO(CH₂)₄NH₂ 4-Me — 3-50 NHCOCH₂NHCH₂Ph 4-Me — 3-51 NHCOCH₂N(CH₂Ph)(CO₂Bu-t) 4-Me — 3-52 NHCOCH₂CH₂OC₆H₄Cl-4 4-Me — 3-53 NHCOCH₂OPh 4-Me — 3-54 NHCOCH₂OC₆H₄F-3 4-Me — 3-55 NHCOCH₂OC₆H₄OCF₃-3 4-Me — 3-56 NHCO(CH₂)₄SMe 4-Me — 3-57 NHCOCH₂CH₂OEt 4-Me — 3-58 NHCOCH₂CH₂OPr-i 4-Me — 3-59 NHCOCH₂CH₂OBu-i 4-Me — 3-60 NHCOCH₂CH₂OCH₂CH₂OMe 4-Me — 3-61 NHCO₂CH₃ 4-Me — 3-62 NHCO₂C₂H₅ 4-Me — 3-63 NHCO₂Pr-n 4-Me — 3-64 NHCO₂Pr-i 4-Me — 3-65 NHCO₂Bu-n 4-Me — 3-66 NHCO₂Bu-i 4-Me — 3-67 NHCO₂Bu-s 4-Me — 3-68 NHCO₂Bu-t 4-i-Pr — 3-69 NHCO₂Bu-t 5-Me — 3-70 NHCO₂Bu-t 4-t-Bu — 3-71 NHCO₂Bu-t 4-Me — 3-72 NHCO₂Bu-t 4-Et — 3-73 NHCO₂Bu-t 4-CHCH₂ — 3-74 NHCO₂Bu-t 4-OMe — 3-75 NHCO₂Bu-t 4-OEt — 3-76 NHCO₂Bu-t 4-OCH₂CH₂OEt — 3-77 NHCO₂Bu-t 4-OPr-i — 3-78 NHCO₂Bu-t 4-OBu-n — 3-79 NHCO₂Bu-t 4-SMe — 3-80 NHCO₂Bu-t 4-SOMe — 3-81 NHCO₂Bu-t 4-SO₂Me — 3-82 NHCO₂Bu-t 4-NMe₂ — 3-83 NHCO₂Bu-t 4-N(Me)(CO₂Bu-t) — 3-84 NHCO₂Bu-t 5-CN — 3-85 NHCO₂Bu-t 4-CN — 3-86 NHCO₂Bu-t 4-morphorino — 3-87 NHCO₂Bu-t 5-Ph — 3-88 NHCO₂Bu-t 5-CO₂C₂H₅ — 3-89 NHCO₂Bu-t 5-CONHCH₃ — 3-90 NHCO₂Bu-t CF₃ — 3-91 NHCO₂Bu-t 5-OH — 3-92 NHCO₂Bu-t 5-SH — 3-93 NHCO₂Bu-t 4-CH₂CI═CI₂ — 3-94 NHCO₂Bu-t 4-etynyl — 3-95 NHCO₂Bu-t 4-propargyl — 3-96 NHCO₂Bu-t 4-(3-iodo-2- — propynyl) 3-97 NHCO₂Bu-t 4-Ph — 3-98 NHCO₂Bu-t 4-C₆H₄OMe-4 — 3-99 NHCO₂Bu-t 4-(2-pyridyl) — 3-100 NHCO₂Bu-t 4-(4-CF₃-2- — oxazolyl) 3-101 NHCO₂Bu-t 4-(3-CF₃-5-Cl-2- — pyridyl) 3-102 NHCO₂Bu-t 4-pyrrolidino — 3-103 NHCO₂Bu-t 4-COMe — 3-104 NHCO₂Bu-t 4-CONHMe — 3-105 NHCO₂Bu-t 4-CONMe₂ — 3-106 NHCO₂Bu-t 4-COPr-c — 3-107 NHCO₂Bu-t 4-COPh — 3-108 NHCO₂Bu-t 4-COCH₂CH═CH₂ — 3-109 NHCO₂Bu-t 4-CO(propargyl) — 3-110 NHCO₂Bu-t 4-CO₂Me — 3-111 NHCO₂Bu-t 4-CO₂Ph — 3-112 NHCO₂Bu-t 4-CO₂CH₂CH═CH₂ — 3-113 NHCO₂Bu-t 4-CO₂(propargyl) — 3-114 NHCO₂Bu-t 4-Me 2-Cl 3-115 NHCO₂Bu-t 4-Me 3-Cl 3-116 NHCO₂Bu-t 4-Me 4-Cl 3-117 NHCO₂Bu-t 4-Me 2,4-Cl₂ 3-118 NHCO₂Bu-t 4-Me 3,5-Cl₂ 3-119 NHCO₂Bu-t 4-Me 3,4,5- Cl₃ 3-120 NHCO₂Bu-t 4-Me 2-Me 3-121 NHCO₂Bu-t 3,4-diMe — 3-122 NHCO₂Bu-t 3,5-diMe — 3-123 NHCO₂Bu-t 4,5-diMe — 3-124 NHCO₂Bu-t 3,4,5-triMe — 3-125 NHCO₂Bu-t 3-Cl-4-Me — 3-126 NHCO₂Bu-t 5-Cl-4-Me — 3-127 NHCO₂Bu-t 3,5-diCl-4-Me — 3-128 NHCO₂Bu-t 3,5-diCl — 3-129 NHCO₂Bu-t 3,4-diCl — 3-130 NHCO₂Bu-t 3,4-diF — 3-131 NHCO₂Bu-n 4-NH₂ — 3-132 NHCO₂Bu-n 4-NHCO₂Bu-t — 3-133 NHCO₂CH₂CF₃ 4-Me — 3-134 NHCO₂C₂F₅ 4-Me — 3-135 NHCO₂CH₂CH₂F 4-Me — 3-136 NHCO₂C(CH₃)₂CF₃ 4-Me — 3-137 NHCO₂CH₂CH₂CF₃ 4-Me — 3-138 NHCO₂CH₂C₂F₅ 4-Me — 3-139 NHCO₂CH₂CH═CH₂ 4-Me — 3-140 NHCO₂CH₂CH═CMe₂ 4-Me — 3-141 NHCO₂C(CH₃)₂CH═CH₂ 4-Me — 3-142 NHCO₂C(CH₃)₂CH═CHCH₃ 4-Me — 3-143 NHCO₂CH₂CH═CHCl 4-Me — 3-144 NHCO₂CH₂CH═CHCF₃ 4-Me — 3-145 NHCO₂CH₂CI═CI₂ 4-Me — 3-146 NHCO₂(1,1-dimethyl-2- 4-Me — propynyl) 3-147 NHCO₂(2-butynyl) 4-Me — 3-148 NHCO₂(1,1-dimethyl-2- 4-Me — butynyl) 3-149 NHCO₂(1,1-dimethyl-2- 4-Me — pentynyl) 3-150 NHCO₂(1-propynyl) 4-Me — 3-151 NHCO₂(1,1-dimethyl-3-Iodo- 4-Me — 2-pentynyl) 3-152 NHCO₂(4,4,4-trifluoro-2- 4-Me — butynyl) 3-153 NHCO₂Pr-c 4-Me — 3-154 NHCO₂Hex-c 4-Me — 3-155 NHCO₂CH₂CH₂NHCO₂Bu-t 4-Me — 3-156 NHCO₂CH₂CH₂NHCO₂Et 4-Me — 3-157 NHCO₂CH₂CH₂CH₂NHCOCH₃ 4-Me — 3-158 NHCO₂CH₂CH₂CH₂NHMe₂ 4-Me — 3-159 NHCO₂CH₂CH₂N(Me)COCH₃ 4-Me — 3-160 NHCO₂CH₂CH₂NHCOPh 4-Me — 3-161 NHCO₂CH₂CH₂N(Me)COPh 4-Me — 3-162 NHCO₂CH₂CH₂NHPh 4-Me — 3-163 NHCO₂(CH₂)₄NH₂ 4-Me — 3-164 NHCO₂CH₂NHCH₂Ph 4-Me — 3-165 NHCO₂CH₂N(CH₂Ph)(CO₂Bu-t) 4-Me — 3-166 NHCO₂CH₂C₃H₅-c 4-Me — 3-167 NHCO₂CH(CH₃)C₃H₅-c 4-Me — 3-168 NHCO₂CH₂C₆H₁₁-c 4-Me — 3-169 NHCO₂CH₂Ph 4-Me — 3-170 NHCO₂CH(CH₃)CH₂Ph 4-Me — 3-171 NHCO₂CH(CH₃)Ph 4-Me — 3-172 NHCO₂C(CH₃)₂Ph 4-Me — 3-173 NHCO₂CH₂C₆H₄CF₃-4 4-Me — 3-174 NHCO₂CH₂C₆H₄CN-4 4-Me — 3-175 NHCO₂CH₂C₆H₄CN-3 4-Me — 3-176 NHCO₂CH₂C₆H₄Cl-4 4-Me — 3-177 NHCO₂CH₂C₆H₄Cl-3 4-Me — 3-178 NHCO₂CH₂C₆H₄OMe-3 4-Me — 3-179 NHCO₂CH₂C₆H₄OMe-2 4-Me — 3-180 NHCO₂CH₂C₆H₄Me-4 4-Me — 3-181 NHCO₂CH₂C₆H₄Me-3 4-Me — 3-182 NHCO₂CH₂C₆H₄Me-2 4-Me — 3-183 NHCO₂CH₂C₆H₄SO₂Me-4 4-Me — 3-184 NHCO₂CH₂C₆H₄SO₂Me-3 4-Me — 3-185 NHCO₂CH₂C₆H₄Ph-4 4-Me — 3-186 NHCO₂CH₂C₆H₄Ph-3 4-Me — 3-187 NHCO₂CH₂Py-2 4-Me — 3-188 NHCO₂CH₂(6-Me-2-Py) 4-Me — 3-189 NHCO₂C(CH₃)₂Py-4 4-Me — 3-190 NHCO₂CH₂(2-thiazolyl) 4-Me — 3-191 NHCO₂CH₂(2-benzthiazolyl) 4-Me — 3-192 NHCO₂CH₂CH₂OMe 4-Me — 3-193 NHCO₂CH₂CH₂OEt 4-Me — 3-194 NHCO₂CH₂CH₂OPr-i 4-Me — 3-195 NHCO₂CH₂CH₂OBu-i 4-Me — 3-196 NHCO₂CH₂CH₂OCH₂CH₂OMe 4-Me — 3-197 NHCO₂CH₂CH₂OEt 4-i-Pr — 3-198 NHCO₂CH₂CH₂OC₆H₄Cl-4 4-Me — 3-199 NHCOCH₂OPh 4-Me — 3-200 NHCOCH₂OC₆H₄F-3 4-Me — 3-201 NHCOCH₂OC₆H₄OCF₃-3 4-Me — 3-202 NHCO₂CH₂CH₂OCH₂Ph 4-Me — 3-203 NHCO₂CH₂CH₂OCH₂CH₂Ph 4-Me — 3-204 NHCO₂(1,1-dimethyl-3- 4-Me — phenyl-2-pentynyl) 3-205 NHCO₂(CH₂)₄SMe 4-Me — 3-206 NHCO₂(CH₂)₄SCF₃ 4-Me — 3-207 NHCO₂(CH₂)₄SPh 4-Me — 3-208 NHCO₂(CH₂)₄SOMe 4-Me — 3-209 NHCO₂(CH₂)₄SOCF₃ 4-Me — 3-210 NHCO₂(CH₂)₄SOPh 4-Me — 3-211 NHCO₂(CH₂)₄SO₂Me 4-Me — 3-212 NHCO₂(CH₂)₄SO₂CF₃ 4-Me — 3-213 NHCO₂(CH₂)₄SO₂Ph 4-Me — 3-214 NHCO₂Ph 4-Me — 3-215 NHCO₂C₆H₄OMe-4 4-Me — 3-216 NHCONHMe 4-Me — 3-217 NHCONHC₂H₅ 4-Me — 3-218 NHCONHPr-n 4-Me — 3-219 NHCONHBu-t 4-Me — 3-220 NHCONHBu-s 4-Me — 3-221 NHCONH(Hex-n) 4-Me — 3-222 H 4-Cl — 3-223 NH₂ 4-Cl — 3-224 NHCHO 4-Cl — 3-225 NHCOCH₂CF₃ 4-Cl — 3-226 NHCOC₂F₅ 4-Cl — 3-227 NHCOCH₂CH₂F 4-Cl — 3-228 NHCOC(CH₃)₂CF₃ 4-Cl — 3-229 NHCOCH₂CH₂CF₃ 4-Cl — 3-230 NHCOCH₂C₂F₅ 4-Cl — 3-231 NHCOCH₂CH═CH₂ 4-Cl — 3-232 NHCOCH₂CH═CMe₂ 4-Cl — 3-233 NHCOC(CH₃)₂CH═CH₂ 4-Cl — 3-234 NHCOC(CH₃)₂CH═CHCH₃ 4-Cl — 3-235 NHCOCH₂CH═CHCl 4-Cl — 3-236 NHCOCH₂CH═CHCF₃ 4-Cl — 3-237 NHCOCH₂CI═CI₂ 4-Cl — 3-238 NHCO(1,1-dimethyl-2- 4-Cl — propynyl) 3-239 NHCO(2-butynyl) 4-Cl — 3-240 NHCO(1,1-dimethyl-2- 4-Cl — butynyl) 3-241 NHCO(1,1-dimethyl-2- 4-Cl — pentynyl) 3-242 NHCO(1-propynyl) 4-Cl — 3-243 NHCO(1,1-dimethyl-3-Iodo- 4-Cl — 2-pentynyl) 3-244 NHCO(4,4,4-trifluoro-2- 4-Cl — butynyl) 3-245 NHCOPr-c 4-Cl — 3-246 NHCOHex-c 4-Cl — 3-247 NHCO(CH₂)₄CO₂H 4-Cl — 3-248 NHCOCH₂CH₂NHCO₂Bu-t 4-Cl — 3-249 NHCOCH₂CH₂NHCO₂Et 4-Cl — 3-250 NHCOCH₂CH₂CH₂NHCOCH₃ 4-Cl — 3-251 NHCOCH₂CH₂CH₂NHMe₂ 4-Cl — 3-252 NHCOCH₂CH₂N(Me)COCH₃ 4-Cl — 3-253 NHCOCH₂CH₂NHCOPh 4-Cl — 3-254 NHCOCH₂CH₂N(Me)COPh 4-Cl — 3-255 NHCOCH₂CH₂NHPh 4-Cl — 3-256 NHCO(CH₂)₄NH₂ 4-Cl — 3-257 NHCOCH₂NHCH₂Ph 4-Cl — 3-258 NHCOCH₂N(CH₂Ph)(CO₂Bu-t) 4-Cl — 3-259 NHCOCH₂CH₂OC₆H₄Cl-4 4-Cl — 3-260 NHCOCH₂OPh 4-Cl — 3-261 NHCOCH₂OC₆H₄F-3 4-Cl — 3-262 NHCOCH₂OC₆H₄OCF₃-3 4-Cl — 3-263 NHCO(CH₂)₄SMe 4-Cl — 3-264 NHCOCH₂CH₂OEt 4-Cl — 3-265 NHCOCH₂CH₂OPr-i 4-Cl — 3-266 NHCOCH₂CH₂OBu-i 4-Cl — 3-267 NHCOCH₂CH₂OCH₂CH₂OMe 4-Cl — 3-268 NHCO₂CH₃ 4-Cl — 3-269 NHCO₂C₂H₅ 4-Cl — 3-270 NHCO₂Pr-n 4-Cl — 3-271 NHCO₂Pr-i 4-Cl — 3-272 NHCO₂Bu-n 4-Cl — 3-273 NHCO₂Bu-i 4-Cl — 3-274 NHCO₂Bu-s 4-Cl — 3-275 NHCO₂Bu-t 4-Cl — 3-276 NHCO₂Bu-t 5-Br — 3-277 NHCO₂Bu-t 5-Cl — 3-278 NHCO₂Bu-t 4-Br — 3-279 NHCO₂Bu-t 4-Cl 2-Cl 3-280 NHCO₂Bu-t 4-Cl 3-Cl 3-281 NHCO₂Bu-t 4-Cl 4-Cl 3-282 NHCO₂Bu-t 4-Cl 2,4-Cl₂ 3-283 NHCO₂Bu-t 4-Cl 3,5-Cl₂ 3-284 NHCO₂Bu-t 4-Cl 3,4,5- Cl₃ 3-285 NHCO₂Bu-t 4-Cl 2-Me 3-286 NHCO₂CH₂CF₃ 4-Cl — 3-287 NHCO₂C₂F₅ 4-Cl — 3-288 NHCO₂CH₂CH₂F 4-Cl — 3-289 NHCO₂C(CH₃)₂CF₃ 4-Cl — 3-290 NHCO₂CH₂CH₂CF₃ 4-Cl — 3-291 NHCO₂CH₂C₂F₅ 4-Cl — 3-292 NHCO₂CH₂CH═CH₂ 4-Cl — 3-293 NHCO₂CH₂CH═CMe₂ 4-Cl — 3-294 NHCO₂C(CH₃)₂CH═CH₂ 4-Cl — 3-295 NHCO₂C(CH₃)₂CH═CHCH₃ 4-Cl — 3-296 NHCO₂CH₂CH═CHCl 4-Cl — 3-297 NHCO₂CH₂CH═CHCF₃ 4-Cl — 3-298 NHCO₂CH₂CI═CI₂ 4-Cl — 3-299 NHCO₂(1,1-dimethyl-2- 4-Cl — propynyl) 3-300 NHCO₂(2-butynyl) 4-Cl — 3-301 NHCO₂(1,1-dimethyl-2- 4-Cl — butynyl) 3-302 NHCO₂(1,1-dimethyl-2- 4-Cl — pentynyl) 3-303 NHCO₂(1-propynyl) 4-Cl — 3-304 NHCO₂(1,1-dimethyl-3-Iodo- 4-Cl — 2-pentynyl) 3-305 NHCO₂(4,4,4-trifluoro-2- 4-Cl — butynyl) 3-306 NHCO₂Pr-c 4-Cl — 3-307 NHCO₂Hex-c 4-Cl — 3-308 NHCO₂CH₂CH₂NHCO₂Bu-t 4-Cl — 3-309 NHCO₂CH₂CH₂NHCO₂Et 4-Cl — 3-310 NHCO₂CH₂CH₂CH₂NHCOCH₃ 4-Cl — 3-311 NHCO₂CH₂CH₂CH₂NMe₂ 4-Cl — 3-312 NHCO₂CH₂CH₂N(Me)COCH₃ 4-Cl — 3-313 NHCO₂CH₂CH₂NHCOPh 4-Cl — 3-314 NHCO₂CH₂CH₂N(Me)COPh 4-Cl — 3-315 NHCO₂CH₂CH₂NHPh 4-Cl — 3-316 NHCO₂(CH₂)₄NH₂ 4-Cl — 3-317 NHCO₂CH₂NHCH₂Ph 4-Cl — 3-318 NHCO₂CH₂N(CH₂Ph)(CO₂Bu-t) 4-Cl — 3-319 NHCO₂CH₂C₃H₅-c 4-Cl — 3-320 NHCO₂CH(CH₃)C₃H₅-c 4-Cl — 3-321 NHCO₂CH₂C₆H₁₁-c 4-Cl — 3-322 NHCO₂CH₂Ph 4-Cl — 3-323 NHCO₂CH₂Ph 5-Cl — 3-324 NHCO₂CH(CH₃)CH₂Ph 4-Cl — 3-325 NHCO₂CH(CH₃)Ph 4-Cl — 3-326 NHCO₂C(CH₃)₂Ph 4-Cl — 3-327 NHCO₂CH₂C₆H₄CF₃-4 4-Cl — 3-328 NHCO₂CH₂C₆H₄CN-4 4-Cl — 3-329 NHCO₂CH₂C₆H₄CN-3 4-Cl — 3-330 NHCO₂CH₂C₆H₄Cl-4 4-Cl — 3-331 NHCO₂CH₂C₆H₄Cl-3 4-Cl — 3-332 NHCO₂CH₂C₆H₄OMe-3 4-Cl — 3-333 NHCO₂CH₂C₆H₄OMe-2 4-Cl — 3-334 NHCO₂CH₂C₆H₄Me-4 4-Cl — 3-335 NHCO₂CH₂C₆H₄Me-3 4-Cl — 3-336 NHCO₂CH₂C₆H₄Me-2 4-Cl — 3-337 NHCO₂CH₂C₆H₄SO₂Me-4 4-Cl — 3-338 NHCO₂CH₂C₆H₄SO₂Me-3 4-Cl — 3-339 NHCO₂CH₂C₆H₄Ph-4 4-Cl — 3-340 NHCO₂CH₂C₆H₄Ph-3 4-Cl — 3-341 NHCO₂CH₂Py-2 4-Cl — 3-342 NHCO₂CH₂(6-Me-2-Py) 4-Cl — 3-343 NHCO₂C(CH₃)₂Py-4 4-Cl — 3-344 NHCO₂CH₂(2-thiazolyl) 4-Cl — 3-345 NHCO₂CH₂(2-benzthiazolyl) 4-Cl — 3-346 NHCO₂CH₂CH₂OMe 4-Cl — 3-347 NHCO₂CH₂CH₂OEt 4-Cl — 3-348 NHCO₂CH₂CH₂OPr-i 4-Cl — 3-349 NHCO₂CH₂CH₂OBu-i 4-Cl — 3-350 NHCO₂CH₂CH₂OCH₂CH₂OMe 4-Cl — 3-351 NHCO₂CH₂CH₂OC₆H₄Cl-4 4-Cl — 3-352 NHCOCH₂OPh 4-Cl — 3-353 NHCOCH₂OC₆H₄F-3 4-Cl — 3-354 NHCOCH₂OC₆H₄OCF₃-3 4-Cl — 3-355 NHCO₂CH₂CH₂OCH₂Ph 4-Cl — 3-356 NHCO₂(1,1-dimethyl-3- 4-Cl — phenyl-2-pentynyl) 3-357 NHCO₂CH₂CH₂OCH₂CH₂Ph 4-Cl — 3-358 NHCO₂(1,1-dimethyl-3- 4-Cl — phenyl-2-pentynyl) 3-359 NHCO₂(CH₂)₄SMe 4-Cl — 3-360 NHCO₂(CH₂)₄SCF₃ 4-Cl — 3-361 NHCO₂(CH₂)₄SPh 4-Cl — 3-362 NHCO₂(CH₂)₄SOMe 4-Cl — 3-363 NHCO₂(CH₂)₄SOCF₃ 4-Cl — 3-364 NHCO₂(CH₂)₄SOPh 4-Cl — 3-365 NHCO₂(CH₂)₄SO₂Me 4-Cl — 3-366 NHCO₂(CH₂)₄SO₂CF₃ 4-Cl — 3-367 NHCO₂(CH₂)₄SO₂Ph 4-Cl — 3-368 NHCO₂Ph 4-Cl — 3-369 NHCO₂C₆H₄OMe-4 4-Cl — 3-370 NHCONHMe 4-Cl — 3-371 NHCONHC₂H₅ 4-Cl — 3-372 NHCONHPr-n 4-Cl — 3-373 NHCONHBu-t 4-Cl — 3-374 NHCONHBu-s 4-Cl — 3-375 NHCONH(Hex-n) 4-Cl — 3-376 NHCOCH₂CF₃ — — 3-377 NHCOC₂F₅ — — 3-378 NHCOCH₂CH₂F — — 3-379 NHCOC(CH₃)₂CF₃ — — 3-380 NHCOCH₂CH₂CF₃ — — 3-381 NHCOCH₂C₂F₅ — — 3-382 NHCOCH₂CH═CH₂ — — 3-383 NHCOCH₂CH═CMe₂ — — 3-384 NHCOC(CH₃)₂CH═CH₂ — — 3-385 NHCOC(CH₃)₂CH═CHCH₃ — — 3-386 NHCOCH₂CH═CHCl — — 3-387 NHCOCH₂CH═CHCF₃ — — 3-388 NHCOCH₂CI═CI₂ — — 3-389 NHCO(1,1-dimethyl-2- — — propynyl) 3-390 NHCO(2-butynyl) — — 3-391 NHCO(1,1-dimethyl-2- — — butynyl) 3-392 NHCO(1,1-dimethyl-2- — — pentynyl) 3-393 NHCO(1-propynyl) — — 3-394 NHCO(1,1-dimethyl-3-Iodo- — — 2-pentynyl) 3-395 NHCO(4,4,4-trifluoro-2- — — butynyl) 3-396 NHCO(CH₂)₄CO₂H — — 3-397 NHCOCH₂CH₂CH₂NHMe₂ — — 3-398 NHCO(CH₂)₄NH₂ — — 3-399 NHCOCH₂NHCH₂Ph — — 3-400 NHCOCH₂N(CH₂Ph)(CO₂Bu-t) — — 3-401 NHCOCH₂CH₂NMe₂ — — 3-402 NHCOCH₂CH₂NHEt — — 3-403 NHCOCH₂CH₂NHPr-n — — 3-404 NHCOCH₂CH₂OC₆H₄Cl-4 — — 3-405 NHCOCH₂OPh — — 3-406 NHCOCH₂OC₆H₄F-3 — — 3-407 NHCOCH₂OC₆H₄OCF₃-3 — — 3-408 NHCOCH₂OC₆H₄CN-2 — — 3-409 NHCOCH₂OC₆H₄F-4 — — 3-410 NHCOCH₂OC₆H₃(3,4- — — methylenedioxy) 3-411 NHCOCH₂OC₆H₄(CONH₂)-2 — — 3-412 NHCOCH₂OC₆H₃(3,4-(OCH₃)₂) — — 3-413 NHCOCH₂O(6-CF₃-pyrimidin- — — 4-yl) 3-414 NHCOCH₂O(3-Py) — — 3-415 NHCO₂CH₂CF₃ — — 3-416 NHCO₂C₂F₅ — — 3-417 NHCO₂CH₂CH₂F — — 3-418 NHCO₂C(CH₃)₂CF₃ — — 3-419 NHCO₂CH₂CH₂CF₃ — — 3-420 NHCO₂CH₂C₂F₅ — — 3-421 NHCO₂CH₂CH═CH₂ — — 3-422 NHCO₂CH₂CH═CMe₂ — — 3-423 NHCO₂C(CH₃)₂CH═CH₂ — — 3-424 NHCO₂C(CH₃)₂CH═CHCH₃ — — 3-425 NHCO₂CH₂CH═CHCl — — 3-426 NHCO₂CH₂CH═CHCF₃ — — 3-427 NHC02CH₂CI═CI₂ — — 3-428 NHCO₂(1,1-dimethyl-2- — — propynyl) 3-429 NHCO₂(2-butynyl) — — 3-430 NHCO₂(1,1-dimethyl-2- — — butynyl) 3-431 NHCO₂(1,1-dimethyl-2- — — pentynyl) 3-432 NHCO₂(1-propynyl) — — 3-433 NHCO₂(1,1-dimethyl-3-Iodo- — — 2-pentynyl) 3-434 NHCO₂(4,4,4-trifluoro-2- — — butynyl) 3-435 NHCO₂(1,1-dimethyl-3 — — phenyl-2-pentynyl) 3-436 NHCO₂CH₂CH₂NHCO₂Bu-t — — 3-437 NHCO₂CH₂CH₂NHCO₂Et — — 3-438 NHCO₂CH₂N(CH₂Ph)(CO₂Bu-t) — — 3-439 NHCO₂CH₂NCH₂Ph — — 3-440 NHCO₂CH₂CH₂NCH₂Ph — — 3-441 NHCO₂CH₂CH₂NCH₂C₆H₄Cl-4 — — 3-442 NHCO₂CH₂CH₂NHMe — — 3-443 NHCO₂CH₂C(CH₃)₂N(CH₃)₂ — — 3-444 NHCO₂CH(CH₃)CH₂N(CH₃)₂ — — 3-445 NHCO₂CH₂C₃H₅-c — — 3-446 NHCO₂CH(CH₃)C₃H₅-c — — 3-447 NHCO₂CH₂C₆H₁₁-c — — 3-448 NHCO₂CH(CH₃)CH₂Ph — — 3-449 NHCO₂CH(CH₃)Ph — — 3-450 NHCO₂C(CH₃)₂Ph — — 3-451 NHCO₂CH₂C₆H₄CF₃-4 — — 3-452 NHCO₂CH₂C₆H₄CN-4 — — 3-453 NHCO₂CH₂C₆H₄CN-3 — — 3-454 NHCO₂CH₂C₆H₄Cl-4 — — 3-455 NHCO₂CH₂C₆H₄Cl-3 — — 3-456 NHCO₂CH₂C₆H₄OMe-3 — — 3-457 NHCO₂CH₂C₆H₄OMe-2 — — 3-458 NHCO₂CH₂C₆H₄Me-4 — — 3-459 NHCO₂CH₂C₆H₄Me-3 — — 3-460 NHCO₂CH₂C₆H₄Me-2 — — 3-461 NHCO₂CH₂C₆H₄SO₂Me-4 — — 3-462 NHCO₂CH₂C₆H₄SO₂Me-3 — — 3-463 NHCO₂CH₂C₆H₄Ph-4 — — 3-464 NHCO₂CH₂C₆H₄Ph-3 — — 3-465 NHCO₂CH₂C₆H₄OCH₃-4 — — 3-466 NHCO₂CH₂C₆H₃(3,4- — — methylenedioxy) 3-467 NHCO₂CH₂Py-2 — — 3-468 NHCO₂CH₂(6-Me-2-Py) — — 3-469 NHCO₂C(CH₃)₂Py-4 — — 3-470 NHCO₂CH₂(2-thiazolyl) — — 3-471 NHCO₂CH₂(2-benzthiazolyl) — — 3-472 NHCO₂CH₂(3-Py) — — 3-473 NHCO₂CH₂(4-Py) — — 3-474 NHCO₂CH(CH₃)(4-Py) — — 3-475 NHCO₂CH₂CH₂OMe — — 3-476 NHCO₂CH₂CH₂OEt — — 3-477 NHCO₂CH₂CH₂OPr-i — — 3-478 NHCO₂CH₂CH₂OBu-i — — 3-479 NHCO₂CH₂CH₂OCH₂CH₂OMe — — 3-480 NHCO₂C(CH₃)₂CH₂OCH₃ — — 3-481 NHCO₂CH(CH₃)CH₂OCH₃ — — 3-482 NHCO₂CH₂CH₂OC₆H₄Cl-4 — — 3-483 NHCO₂CH₂OPh — — 3-484 NHCO₂CH₂OC₆H₄F-3 — — 3-485 NHCO₂CH₂OC₆H₄OCF₃-3 — — 3-486 NHCO₂CH₂CH₂OCH₂Ph — — 3-487 NHCO₂CH₂CH₂OCH₂CH₂Ph — — 3-488 NHCO₂(CH₂)₄SMe — — 3-489 NHCO₂(CH₂)₄SCF₃ — — 3-490 NHCO₂(CH₂)₄SPh — — 3-491 NHCO₂(CH₂)₄SOMe — — 3-492 NHCO₂(CH₂)₄SOCF₃ — — 3-493 NHCO₂(CH₂)₄SOPh — — 3-494 NHCO₂(CH₂)₄SO₂Me — — 3-495 NHCO₂(CH₂)₄SO₂CF₃ — — 3-496 NHCO₂(CH₂)₄SO₂Ph — — 3-497 NHCO₂Ph — — 3-498 NHCO₂C₆H₄OMe-4 — — 3-499 NHCOCH₂CH₂CH₂COCH₃ — —

TABLE 4

mp ° No Z¹¹ R¹¹ (X)_(n1) C. 4-1 H Me — 4-2 NH₂ Me — 4-3 NH₂ Bu-t — 4-4 NH₂ OC₂H₅ — 4-5 NH₂ OCH₃ — 4-6 NH₂ C₂H₅ — 4-7 NHCHO Me — 4-8 NHCOCH₃ Me — 4-9 NHCOC₂H₅ Me — 4-10 NHCOPr-n Me — 4-11 NHCOPr-i Me — 4-12 NHCOBu-n Me — 4-13 NHCOBu-i Me — 4-14 NHCOBu-s Me — 4-15 NHCOBu-t Me — 4-16 NHCOBu-t OMe — 4-17 NHCOCH₂CF₃ Me — 4-18 NHCOC₂F₅ Me — 4-19 NHCOCH₂CH₂F Me — 4-20 NHCOC(CH₃)₂CF₃ Me — 4-21 NHCOCH₂CH₂CF₃ Me — 4-22 NHCOCH₂C₂F₅ Me — 4-23 NHCOCH₂CH═CH₂ Me — 4-24 NHCOCH₂CH═CMe₂ Me — 4-25 NHCOC(CH₃)₂CH═CH₂ Me — 4-26 NHCOC(CH₃)₂CH═CHCH₃ Me — 4-27 NHCOCH₂CH═CHCl Me — 4-28 NHCOCH₂CH═CHCF₃ Me — 4-29 NHCOCH₂CI═CI₂ Me — 4-30 NHCO(1,1-dimethyl-2- Me — propynyl) 4-31 NHCO(2-butynyl) Me — 4-32 NHCO(1,1-dimethyl-2-butynyl) Me — 4-33 NHCO(1,1-dimethyl-2-pentynyl) Me — 4-34 NHCO(1-propynyl) Me — 4-35 NHCO(1,1-dimethyl-3-Iodo-2- Me — pentynyl) 4-36 NHCO(4,4,4-trifluoro-2- Me — butynyl) 4-37 NHCOPr-c Me — 4-38 NHCOHex-c Me — 4-39 NHCO(CH₂)₄CO₂H Me — 4-40 NHCOCH₂CH₂NHCO₂Bu-t Me — 4-41 NHCOCH₂CH₂NHCO₂Et Me — 4-42 NHCOCH₂CH₂CH₂NHCOCH₃ Me — 4-43 NHCOCH₂CH₂CH₂NHMe₂ Me — 4-44 NHCOCH₂CH₂M(Me)COCH₃ Me — 4-45 NHCOCH₂CH₂NHCOPh Me — 4-46 NHCOCH₂CH₂N(Me)COPh Me — 4-47 NHCOCH₂CH₂NHPh Me — 4-48 NHCO(CH₂)₄NH₂ Me — 4-49 NHCOCH₂NHCH₂Ph Me — 4-50 NHCOCH₂N(CH₂Ph)(CO₂Bu-t) Me — 4-51 NHCOCH₂CH₂OC₆H₄Cl-4 Me — 4-52 NHCOCH₂OPh Me — 4-53 NHCOCH₂OC₆H₄F-3 Me — 4-54 NHCOCH₂OC₆H₄OCF₃-3 Me — 4-55 NHCO(CH₂)₄SMe Me — 4-56 NHCOCH₂CH₂OEt Me — 4-57 NHCOCH₂CH₂OPr-i Me — 4-58 NHCOCH₂CH₂OBu-i Me — 4-59 NHCOCH₂CH₂OCH₂CH₂OMe Me — 4-60 NHCO₂CH₃ Me — 4-61 NHCO₂C₂H₅ Me — 4-62 NHCO₂Pr-n Me — 4-63 NHCO₂Pr-i Me — 4-64 NHCO₂Bu-n Me — 4-65 NHCO₂Bu-i Me — 4-66 NHCO₂Bu-s Me — 4-67 NHCO₂Bu-t i-Pr — 4-68 NHCO₂Bu-t Me — 4-69 NHCO₂Bu-t t-Bu — 4-70 NHCO₂Bu-t Et — 4-71 NHCO₂Bu-t CH═CH2 — 4-72 NHCO₂Bu-t OMe — 4-73 NHCO₂Bu-t OEt — 4-74 NHCO₂Bu-t OCH₂CH₂OEt — 4-75 NHCO₂Bu-t OPr-i — 4-76 NHCO₂Bu-t OBu-n — 4-77 NHCO₂Bu-t SMe — 4-78 NHCO₂Bu-t SOMe — 4-79 NHCO₂Bu-t SO₂Me — 4-80 NHCO₂Bu-t NMe₂ — 4-81 NHCO₂Bu-t N(Me)(CO₂Bu-t) — 4-82 NHCO₂Bu-t CN — 4-83 NHCO₂Bu-t morphorino — 4-84 NHCO₂Bu-t Ph — 4-85 NHCO₂Bu-t CO₂C₂H₅ — 4-86 NHCO₂Bu-t CONHCH₃ — 4-87 NHCO₂Bu-t CF₃ — 4-88 NHCO₂Bu-t OH — 4-89 NHCO₂Bu-t SH — 4-90 NHCO₂Bu-t CH₂CI═CI₂ — 4-91 NHCO₂Bu-t etynyl — 4-92 NHCO₂Bu-t propargyl — 4-93 NHCO₂Bu-t (3-iodo-2-propynyl) — 4-94 NHCO₂Bu-t Ph — 4-95 NHCO₂Bu-t C₆H₄OMe-4 — 4-96 NHCO₂Bu-t 2-pyridyl — 4-97 NHCO₂Bu-t 4-CF₃-2-oxazolyl — 4-98 NHCO₂Bu-t 3-CF₃-5-Cl-2- — pyridyl 4-99 NHCO₂Bu-t pyrrolidino — 4-100 NHCO₂Bu-t COMe — 4-101 NHCO₂Bu-t CONHMe — 4-102 NHCO₂Bu-t CONMe₂ — 4-103 NHCO₂Bu-t COPr-c — 4-104 NHCO₂Bu-t COPh — 4-105 NHCO₂Bu-t COCH₂CH═CH₂ — 4-106 NHCO₂Bu-t CO(propargyl) — 4-107 NHCO₂Bu-t CO₂Me — 4-108 NHCO₂Bu-t CO₂Ph — 4-109 NHCO₂Bu-t CO₂CH₂CH═CH₂ — 4-110 NHCO₂Bu-t CO₂(propargyl) — 4-111 NHCO₂Bu-t Me 2-Cl 4-112 NHCO₂Bu-t Me 3-Cl 4-113 NHCO₂Bu-t Me 4-Cl 4-114 NHCO₂Bu-t Me 2,4- Cl₂ 4-115 NHCO₂Bu-t Me 3,5- Cl₂ 4-116 NHCO₂Bu-t Me 3,4,5- Cl₃ 4-117 NHCO₂Bu-t Me 2-Me 4-118 NHCO₂Bu-n NH₂ — 4-119 NHCO₂Bu-n NHCO₂Bu-t — 4-120 NHCO₂CH₂CF₃ Me — 4-121 NHCO₂C₂F₅ Me — 4-122 NHCO₂CH₂CH₂F Me — 4-123 NHCO₂C(CH₃)₂CF₃ Me — 4-124 NHCO₂CH₂CH₂CF₃ Me — 4-125 NHCO₂CH₂C₂F₅ Me — 4-126 NHCO₂CH₂CH═CH₂ Me — 4-127 NHCO₂CH₂CH═CMe₂ Me — 4-128 NHCO₂C(CH₃)₂CH═CH₂ Me — 4-129 NHCO₂C(CH₃)₂CH═CHCH₃ Me — 4-130 NHCO₂CH₂CH═CHCl Me — 4-131 NHCO₂CH₂CH═CHCF₃ Me — 4-132 NHCO₂CH₂CI═CI₂ Me — 4-133 NHCO₂(1,1-dimethyl-2- Me — propynyl) 4-134 NHCO₂(2-butynyl) Me — 4-135 NHCO₂(1,1-dimethyl-2-butynyl) Me — 4-136 NHCO₂(1,1-dimethyl-2- Me — pentynyl) 4-137 NHCO₂(1-propynyl) Me — 4-138 NHCO₂(1,1-dimethyl-3-Iodo-2- Me — pentynyl) 4-139 NHCO₂(4,4,4-trifluoro-2- Me — butynyl) 4-140 NHCO₂Pr-c Me — 4-141 NHCO₂Hex-c Me — 4-142 NHCO₂CH₂CH₂NHCO₂Bu-t Me — 4-143 NHCO₂CH₂CH₂NHCO₂Et Me — 4-144 NHCO₂CH₂CH₂CH₂NHCOCH₃ Me — 4-145 NHCO₂CH₂CH₂CH₂NHMe₂ Me — 4-146 NHCO₂CH₂CH₂N(Me)COCH₃ Me — 4-147 NHCO₂CH₂CH₂NHCOPh Me — 4-148 NHCO₂CH₂CH₂N(Me)COPh Me — 4-149 NHCO₂CH₂CH₂NHPh Me — 4-150 NHCO₂(CH₂)₄NH₂ Me — 4-151 NHCO₂CH₂NHCH₂Ph Me — 4-152 NHCO₂CH₂N(CH₂Ph)(CO₂Bu- Me — t) 4-153 NHCO₂CH₂C₃H₅-c Me — 4-154 NHCO₂CH(CH₃)C₃H₅-c Me — 4-155 NHCO₂CH₂C₆H₁₁-c Me — 4-156 NHCO₂CH₂Ph Me — 4-157 NHCO₂CH(CH₃)CH₂Ph Me — 4-158 NHCO₂CH(CH₃)Ph Me — 4-159 NHCO₂C(CH₃)₂Ph Me — 4-160 NHCO₂CH₂C₆H₄CF₃-4 Me — 4-161 NHCO₂CH₂C₆H₄CN-4 Me — 4-162 NHCO₂CH₂C₆H₄CN-3 Me — 4-163 NHCO₂CH₂C₆H₄Cl-4 Me — 4-164 NHCO₂CH₂C₆H₄Cl-3 Me — 4-165 NHCO₂CH₂C₆H₄OMe-3 Me — 4-166 NHCO₂CH₂C₆H₄OMe-2 Me — 4-167 NHCO₂CH₂C₆H₄Me-4 Me — 4-168 NHCO₂CH₂C₆H₄Me-3 Me — 4-169 NHCO₂CH₂C₆H₄Me-2 Me — 4-170 NHCO₂CH₂C₆H₄SO₂Me-4 Me — 4-171 NHCO₂CH₂C₆H₄SO₂Me-3 Me — 4-172 NHCO₂CH₂C₆H₄Ph-4 Me — 4-173 NHCO₂CH₂C₆H₄Ph-3 Me — 4-174 NHCO₂CH₂Py-2 Me — 4-175 NHCO₂CH₂(6-Me-2-Py) Me — 4-176 NHCO₂C(CH₃)₂Py-4 Me — 4-177 NHCO₂CH₂(2-thiazolyl) Me — 4-178 NHCO₂CH₂(2-benzthiazolyl) Me — 4-179 NHCO₂CH₂CH₂OMe Me — 4-180 NHCO₂CH₂CH₂OEt Me — 4-181 NHCO₂CH₂CH₂OPr-i Me — 4-182 NHCO₂CH₂CH₂OBu-i Me — 4-183 NHCO₂CH₂CH₂OCH₂CH₂OMe Me — 4-184 NHCO₂CH₂CH₂OEt i-Pr — 4-185 NHCO₂CH₂CH₂OC₆H₄Cl-4 Me — 4-186 NHCOCH₂OPh Me — 4-187 NHCOCH₂OC₆H₄F-3 Me — 4-188 NHCOCH₂OC₆H₄OCF₃-3 Me — 4-189 NHCO₂CH₂CH₂OCH₂Ph Me — 4-190 NHCO₂CH₂CH₂OCH₂CH₂Ph Me — 4-191 NHCO₂(1,1-dimethyl-3-phenyl- Me — 2-pentynyl) 4-192 NHCO₂(CH₂)₄SMe Me — 4-193 NHCO₂(CH₂)₄SCF₃ Me — 4-194 NHCO₂(CH₂)₄SPh Me — 4-195 NHCO₂(CH₂)₄SOMe Me — 4-196 NHCO₂(CH₂)₄SOCF₃ Me — 4-197 NHCO₂(CH₂)₄SOPh Me — 4-198 NHCO₂(CH₂)₄SO₂Me Me — 4-199 NHCO₂(CH₂)₄SO₂CF₃ Me — 4-200 NHCO₂(CH₂)₄SO₂Ph Me — 4-201 NHCO₂Ph Me — 4-202 NHCO₂C₆H₄OMe-4 Me — 4-203 NHCONHMe Me — 4-204 NHCONHC₂H₅ Me — 4-205 NHCONHPr-n Me — 4-206 NHCONHBu-t Me — 4-207 NHCONHBu-s Me — 4-208 NHCONH(Hex-n) Me — 4-209 H Cl — 4-210 NH₂ Cl — 4-211 NHCHO Cl — 4-212 NHCOCH₂CF₃ Cl — 4-213 NHCOC₂F₅ Cl — 4-214 NHCOCH₂CH₂F Cl — 4-215 NHCOC(CH₃)₂CF₃ Cl — 4-216 NHCOCH₂CH₂CF₃ Cl — 4-217 NHCOCH₂C₂F₅ Cl — 4-218 NHCOCH₂CH═CH₂ Cl — 4-219 NHCOCH₂CH═CMe₂ Cl — 4-220 NHCOC(CH₃)₂CH═CH₂ Cl — 4-221 NHCOC(CH₃)₂CH═CHCH₃ Cl — 4-222 NHCOCH₂CH═CHCl Cl — 4-223 NHCOCH₂CH═CHCF₃ Cl — 4-224 NHCOCH₂CI₂ Cl — 4-225 NHCO(1,1-dimethyl-2- Cl — propynyl) 4-226 NHCO(2-butynyl) Cl — 4-227 NHCO(1,1-dimethyl-2-butynyl) Cl — 4-228 NHCO(1,1-dimethyl-2-pentynyl) Cl — 4-229 NHCO(1-propynyl) Cl — 4-230 NHCO(1,1-dimethyl-3-Iodo-2- Cl — pentynyl) 4-231 NHCO(4,4,4-trifluoro-2- Cl — butynyl) 4-232 NHCOPr-c Cl — 4-233 NHCOHex-c Cl — 4-234 NHCO(CH₂)₄CO₂H Cl — 4-235 NHCOCH₂CH₂NHCO₂Bu-t Cl — 4-236 NHCOCH₂CH₂NHCO₂Et Cl — 4-237 NHCOCH₂CH₂CH₂NHCOCH₃ Cl — 4-238 NHCOCH₂CH₂CH₂NHMe₂ Cl — 4-239 NHCOCH₂CH₂N(Me)COCH₃ Cl — 4-240 NHCOCH₂CH₂NHCOPh Cl — 4-241 NHCOCH₂CH₂N(Me)COPh Cl — 4-242 NHCOCH₂CH₂NHPh Cl — 4-243 NHCO(CH₂)₄NH₂ Cl — 4-244 NHCOCH₂NHCH₂Ph Cl — 4-245 NHCOCH₂N(CH₂Ph)(CO₂Bu-t) Cl — 4-246 NHCOCH₂CH₂OC₆H₄Cl-4 Cl — 4-247 NHCOCH₂OPh Cl — 4-248 NHCOCH₂OC₆H₄F-3 Cl — 4-249 NHCOCH₂OC₆H₄OCF₃-3 Cl — 4-250 NHCO(CH₂)₄SMe Cl — 4-251 NHCOCH₂CH₂OEt Cl — 4-252 NHCOCH₂CH₂OPr-i Cl — 4-253 NHCOCH₂CH₂OBu-i Cl — 4-254 NHCOCH₂CH₂OCH₂CH₂OMe Cl — 4-255 NHCO₂CH₃ Cl — 4-256 NHCO₂C₂H₅ Cl — 4-257 NHCO₂Pr-n Cl — 4-258 NHCO₂Pr-i Cl — 4-259 NHCO₂Bu-n Cl — 4-260 NHCO₂Bu-i Cl — 4-261 NHCO₂Bu-s Cl — 4-262 NHCO₂Bu-t Cl — 4-263 NHCO₂Bu-t Br — 4-264 NHCO₂Bu-t Cl 2-Cl 4-265 NHCO₂Bu-t Cl 3-Cl 4-266 NHCO₂Bu-t Cl 4-Cl 4-267 NHCO₂Bu-t Cl 2,4- Cl₂ 4-268 NHCO₂Bu-t Cl 3,5- Cl₂ 4-269 NHCO₂Bu-t Cl 3,4,5- Cl₃ 4-270 NHCO₂Bu-t Cl 2-Me 4-271 NHCO₂CH₂CF₃ Cl — 4-272 NHCO₂C₂F₅ Cl — 4-273 NHCO₂CH₂CH₂F Cl — 4-274 NHCO₂C(CH₃)₂CF₃ Cl — 4-275 NHCO₂CH₂CH₂CF₃ Cl — 4-276 NHCO₂C₂F₅ Cl — 4-277 NHCO₂CH═CH₂ Cl — 4-278 NHCO₂CH═CMe₂ Cl — 4-279 NHCO₂C(CH₃)₂CH═CH₂ Cl — 4-280 NHCO₂C(CH₃)₂CH═CHCH₃ Cl — 4-281 NHCO₂CH₂CH═CHCl Cl — 4-282 NHCO₂CH₂CH═CHCF₃ Cl — 4-283 NHCO₂CH₂CI═CI₂ Cl — 4-284 NHCO₂(1,1-dimethyl-2- Cl — propynyl) 4-285 NHCO₂(2-butynyl) Cl — 4-286 NHCO₂(1,1-dimethyl-2-butynyl) Cl — 4-287 NHCO₂(1,1-dimethyl-2- Cl — pentynyl) 4-288 NHCO₂(1-propynyl) Cl — 4-289 NHCO₂(1,1-dimethyl-3-Iodo-2- Cl — pentynyl) 4-290 NHCO₂(4,4,4-trifluoro-2- Cl — butynyl) 4-291 NHCO₂Pr-c Cl — 4-292 NHCO₂Hex-c Cl — 4-293 NHCO₂CH₂CH₂NHCO₂Bu-t Cl — 4-294 NHCO₂CH₂CH₂NHCO₂Et Cl — 4-295 NHCO₂CH₂CH₂CH₂NHCOCH₃ Cl — 4-296 NHCO₂CH₂CH₂CH₂NMe₂ Cl — 4-297 NHCO₂CH₂CH₂N(Me)COCH₃ Cl — 4-298 NHCO₂CH₂CH₂NHCOPh Cl — 4-299 NHCO₂CH₂CH₂N(Me)COPh Cl — 4-300 NHCO₂CH₂CH₂NHPh Cl — 4-301 NHCO₂(CH₂)₄NH₂ Cl — 4-302 NHCO₂CH₂NHCH₂Ph Cl — 4-303 NHCO₂CH₂N(CH₂Ph)(CO₂Bu- Cl — t) 4-304 NHCO₂CH₂C₃H₅-c Cl — 4-305 NHCO₂CH(CH₃)C₃H₅-c Cl — 4-306 NHCO₂CH₂C₆H₁₁-c Cl — 4-307 NHCO₂CH₂Ph Cl — 4-308 NHCO₂CH(CH₃)CH₂Ph Cl — 4-309 NHCO₂CH(CH₃)Ph Cl — 4-310 NHCO₂C(CH₃)₂Ph Cl — 4-311 NHCO₂CH₂C₆H₄CF₃-4 Cl — 4-312 NHCO₂CH₂C₆H₄CN-4 Cl — 4-313 NHCO₂CH₂C₆H₄CN-3 Cl — 4-314 NHCO₂CH₂C₆H₄Cl-4 Cl — 4-315 NHCO₂CH₂C₆H₄Cl-3 Cl — 4-316 NHCO₂CH₂C₆H₄OMe-3 Cl — 4-317 NHCO₂CH₂C₆H₄OMe-2 Cl — 4-318 NHCO₂CH₂C₆H₄Me-4 Cl — 4-319 NHCO₂CH₂C₆H₄Me-3 Cl — 4-320 NHCO₂CH₂C₆H₄Me-2 Cl — 4-321 NHCO₂CH₂C₆H₄SO₂Me-4 Cl — 4-322 NHCO₂CH₂C₆H₄SO₂Me-3 Cl — 4-323 NHCO₂CH₂C₆H₄Ph-4 Cl — 4-324 NHCO₂CH₂C₆H₄Ph-3 Cl — 4-325 NHCO₂CH₂Py-2 Cl — 4-326 NHCO₂CH₂(6-Me-2-Py) Cl — 4-327 NHCO₂C(CH₃)₂Py-4 Cl — 4-328 NHCO₂CH₂(2-thiazolyl) Cl — 4-329 NHCO₂CH₂(2-benzthiazolyl) Cl — 4-330 NHCO₂CH₂CH₂OMe Cl — 4-331 NHCO₂CH₂CH₂OEt Cl — 4-332 NHCO₂CH₂CH₂OPr-i Cl — 4-333 NHCO₂CH₂CH₂OBu-i Cl — 4-334 NHCO₂CH₂CH₂OCH₂CH₂OMe Cl — 4-335 NHCO₂CH₂CH₂OC₆H₄Cl-4 Cl — 4-336 NHCOCH₂OPh Cl — 4-337 NHCOCH₂OC₆H₄F-3 Cl — 4-338 NHCOCH₂OC₆H₄OCF₃-3 Cl — 4-339 NHCO₂CH₂CH₂OCH₂Ph Cl — 4-340 NHCO₂(1,1-dimethyl-3-phenyl- Cl — 2-pentynyl) 4-341 NHCO₂CH₂CH₂OCH₂CH₂Ph Cl — 4-342 NHCO₂(1,1-dimethyl-3-phenyl- Cl — 2-pentynyl) 4-343 NHCO₂(CH₂)₄SMe Cl — 4-344 NHCO₂(CH₂)₄SCF₃ Cl — 4-345 NHCO₂(CH₂)₄SPh Cl — 4-346 NHCO₂(CH₂)₄SOMe Cl — 4-347 NHCO₂(CH₂)₄SOCF₃ Cl — 4-348 NHCO₂(CH₂)₄SOPh Cl — 4-349 NHCO₂(CH₂)₄SO₂Me Cl — 4-350 NHCO₂(CH₂)₄SO₂CF₃ Cl — 4-351 NHCO₂(CH₂)₄SO₂Ph Cl — 4-352 NHCO₂Ph Cl — 4-353 NHCO₂C₆H₄OMe-4 Cl — 4-354 NHCONHMe Cl — 4-355 NHCONHC₂H₅ Cl — 4-356 NHCONHPr-n Cl — 4-357 NHCONHBu-t Cl — 4-358 NHCONHBu-s Cl — 4-359 NHCONH(Hex-n) Cl — 4-360 NHCOCH₂CF₃ — — 4-361 NHCOC₂F₅ — — 4-362 NHCOCH₂CH₂F — — 4-363 NHCOC(CH₃)₂CF₃ — — 4-364 NHCOCH₂CH₂CF₃ — — 4-365 NHCOCH₂C₂F₅ — — 4-366 NHCOCH₂CH═CH₂ — — 4-367 NHCOCH₂CH═CMe₂ — — 4-368 NHCOC(CH₃)₂CH═CH₂ — — 4-369 NHCOC(CH₃)₂CH═CHCH₃ — — 4-370 NHCOCH₂CH═CHCl — — 4-371 NHCOCH₂CH═CHCF₃ — — 4-372 NHCOCH₂CI═CI₂ — — 4-373 NHCO(1,1-dimethyl-2- — — propynyl) 4-374 NHCO(2-butynyl) — — 4-375 NHCO(1,1-dimethyl-2-butynyl) — — 4-376 NHCO(1,1-dimethyl-2-pentynyl) — — 4-377 NHCO(1-propynyl) — — 4-378 NHCO(1,1-dimethyl-3-Iodo-2- pentynyl) 4-379 NHCO(4,4,4-trifluoro-2- — — butynyl) 4-380 NHCO(CH₂)₄CO₂H — — 4-381 NHCOCH₂CH₂CH₂NHMe₂ — — 4-382 NHCO(CH₂)₄NH₂ — — 4-383 NHCOCH₂NHCH₂Ph — — 4-384 NHCOCH₂N(CH₂Ph)(CO₂Bu-t) — — 4-385 NHCOCH₂CH₂NMe₂ — — 4-386 NHCOCH₂CH₂NHEt — — 4-387 NHCOCH₂CH₂NHPr-n — — 4-388 NHCOCH₂CH₂OC₆H₄Cl-4 — — 4-389 NHCOCH₂OPh — — 4-390 NHCOCH₂OC₆H₄F-3 — — 4-391 NHCOCH₂OC₆H₄OCF₃-3 — — 4-392 NHCOCH2OC₆H₄CN-2 — — 4-393 NHCOCH2OC₆H₄F-4 — — 4-394 NHCOCH₂OC₆H₃(3,4- — — methylenedioxy) 4-395 NHCOCH₂OC₆H₄(CONH₂)-2 — — 4-396 NHCOCH₂OC₆H₃(3,4-(OCH₃)₂) — — 4-397 NHCOCH₂O(6-CF₃-pyrimidin- — — 4-yl) 4-398 NHCOCH₂O(3-Py) — — 4-399 NHCOCH₂CH₂CH₂COCH₃ — — 4-400 NHCO₂CH₂CF₃ — — 4-401 NHCO₂C₂F₅ — — 4-402 NHCO₂CH₂CH₂F — — 4-403 NHCO₂C(CH₃)₂CF₃ — — 4-404 NHCO₂CH₂CH₂CF₃ — — 4-405 NHCO₂CH₂C₂F₅ — — 4-406 NHCO₂CH₂CH═CH₂ — — 4-407 NHCO₂CH₂CH═CMe₂ — — 4-408 NHCO₂C(CH₃)₂CH═CH₂ — — 4-409 NHCO₂C(CH₃)₂CH═CHCH₃ — — 4-410 NHCO₂CH₂CH═CHCl — — 4-411 NHCO₂CH₂CH═CHCF₃ — — 4-412 NHCO₂CH₂CI═CI₂ — — 4-413 NHCO₂(1,1-dimethyl-2- — — propynyl) 4-414 NHCO₂(2-butynyl) — — 4-415 NHCO₂(1,1-dimethyl-2-butynyl) — — 4-416 NHCO₂(1,1-dimethyl-2- — — pentynyl) 4-417 NHCO₂(1-propynyl) — — 4-418 NHCO₂(1,1-dimethyl-3-Iodo-2- — — pentynyl) 4-419 NHCO₂(4,4,4-trifluoro-2- — — butynyl) 4-420 NHCO₂(1,1-dimethyl-3-phenyl- — — 2-pentynyl) 4-421 NHCO₂CH₂CH₂NHCO₂Bu-t — — 4-422 NHCO₂CH₂CH₂NHCO₂Et — — 4-423 NHCO₂CH₂N(CH₂Ph)(CO₂Bu- — — t) 4-424 NHCO₂CH₂NCH₂Ph — — 4-425 NHCO₂CH₂CH₂NCH₂Ph — — 4-426 NHCO₂CH₂CH₂NCH₂C₆H₄Cl-4 — — 4-427 NHCO₂CH₂CH₂NHMe — — 4-428 NHCO₂CH₂C(CH₃)₂N(CH₃)₂ — — 4-429 NHCO₂CH(CH₃)CH₂N(CH₃)₂ — — 4-430 NHCO₂CH₂C₃H₅-c — — 4-431 NHCO₂CH(CH₃)C₃H₅-c — — 4-432 NHCO₂CH₂C₆H₁₁-c — — 4-433 NHCO₂CH(CH₃)CH₂Ph — — 4-434 NHCO₂CH(CH₃)Ph — — 4-435 NHCO₂C(CH₃)₂Ph — — 4-436 NHCO₂CH₂C₆H₄CF₃-4 — — 4-437 NHCO₂CH₂C₆H₄CN-4 — — 4-438 NHCO₂CH₂C₆H₄CN-3 — — 4-439 NHCO₂CH₂C₆H₄Cl-4 — — 4-440 NHCO₂CH₂C₆H₄Cl-3 — — 4-441 NHCO₂CH₂C₆H₄OMe-3 — — 4-442 NHCO₂CH₂C₆H₄OMe-2 — — 4-443 NHCO₂CH₂C₆H₄Me-4 — — 4-444 NHCO₂CH₂C₆H₄Me-3 — — 4-445 NHCO₂CH₂C₆H₄Me-2 — — 4-446 NHCO₂CH₂C₆H₄SO₂Me-4 — — 4-447 NHCO₂CH₂C₆H₄SO₂Me-3 — — 4-448 NHCO₂CH₂C₆H₄Ph-4 — — 4-449 NHCO₂CH₂C₆H₄Ph-3 — — 4-450 NHCO₂CH₂C₆H₄OCH₃-4 — — 4-451 NHCO₂CH₂C₆H₃(3,4- methylenedioxy) 4-452 NHCO₂CH₂Py-2 — — 4-453 NHCO₂CH₂(6-Me-2-Py) — — 4-454 NHCO₂C(CH₃)₂Py-4 — — 4-455 NHCO₂CH₂(2-thiazolyl) — — 4-456 NHCO₂CH₂(2-benzthiazolyl) — — 4-457 NHCO₂CH₂(3-Py) — — 4-458 NHCO₂CH₂(4-Py) — — 4-459 NHCO₂CH(CH₃)(4-Py) — — 4-460 NHCO₂CH₂CH₂OMe — — 4-461 NHCO₂CH₂CH₂OEt — — 4-462 NHCO₂CH₂CH₂OPr-i — — 4-463 NHCO₂CH₂CH₂OBu-i — — 4-464 NHCO₂CH₂CH₂OCH₂CH₂OMe — — 4-465 NHCO₂C(CH₃)₂CH₂OCH₃ — — 4-466 NHCO₂CH(CH₃)CH₂OCH₃ — — 4-467 NHCO₂CH₂CH₂OC₆H₄Cl-4 — — 4-468 NHCO₂CH₂OPh — — 4-469 NHCO₂CH₂OC₆H₄F-3 — — 4-470 NHCO₂CH₂OC₆H₄OCF₃-3 — — 4-471 NHCO₂CH₂CH₂OCH₂Ph — — 4-472 NHCO₂CH₂CH₂OCH₂CH₂Ph — — 4-473 NHCO₂(CH₂)₄SMe — — 4-474 NHCO₂(CH₂)₄SCF₃ — — 4-475 NHCO₂(CH₂)₄SPh — — 4-476 NHCO₂(CH₂)₄SOMe — — 4-477 NHCO₂(CH₂)₄SOCF₃ — — 4-478 NHCO₂(CH₂)₄SOPh — — 4-479 NHCO₂(CH₂)₄SO₂Me — — 4-480 NHCO₂(CH₂)₄SO₂CF₃ — — 4-481 NHCO₂(CH₂)₄SO₂Ph — — 4-482 NHCO₂Ph — — 4-483 NHCO₂C₆H₄OMe-4 — —

Among the compounds shown in Tables 1 to 4, the spectral data (¹H-NMR (300 MHz, CDCl₃)) of some compounds are as shown in Table 5.

TABLE 5 No NMR Data 1-3 1.24 (s, 9H), 4.01 (s, 3H), 4.37 (br-s, 2H), 5.21 (s, 2H), 6.41 (d, 1H, J = 1.1 Hz), 6.63 (d, 1H, J = 1.1 Hz), 7.34-7.44 (m, 3H), 7.53-7.56 (m, 2H). 1-4 1.38 (t, 3H, J = 7.0 Hz), 3.97-4.04 (m, 2H), 4.01 (s, 3H), 4.35 (br-s, 2H), 5.16 (s, 2H), 5.88 (d, 1H, J = 2.0 Hz), 6.20 (d, 1H, J = 2.0 Hz), 7.35-7.44 (m, 3H), 7.52-7.55 (m, 2H). 1-5 2.19 (s, 3H), 3.96 (s, 3H), 4.29 (br-s, 2H), 5.27 (s, 2H), 6.42 (d, 1H, J = 8.2 Hz), 7.23-7.26 (m, 1H), 7.34-7.46 (m, 3H), 7.51-7.54 (m, 2H). 1-6 3.77 (s, 3H), 4.00 (s, 3H), 4.40 (br-s, 2H), 5.16 (s, 2H), 5.89 (s, 1H), 6.21 (s, 1H), 7.34-7.54 (m, 5H) 1-7 1.19 (t, 3H), 2.52 (q, 2H), 4.00 (s, 3H), 4.45 (br-s, 2H), 5.19 (s, 2H), 6.29 (s, 1H), 6.47 (s, 1H), 7.34-7.55 (m, 5H) 1-17 1.33 (s, 9H), 3.85 (s, 3H), 3.99 (s, 3H), 5.20 (s, 2H), 6.54 (d, 1H, J = 2.1 Hz), 7.34-7.53 (m, 5H), 7.82 (d, 1H, J = 2.1 Hz), 7.95 (br-s, 1H). 1-71 1.52 (s, 9H), 2.33 (s, 3H), 3.97 (s, 3H), 5.21 (s, 2H), 6.75 (s, 1H), 7.13 (br-s, 1H), 7.34-7.54 (m, 5H), 7.71 (s, 1H). 1-73 1.53 (s, 9H), 3.98 (s, 3H), 5.24 (s, 2H), 5.48 (d, 1H, J = 11.1 Hz), 5.99 (d, 1H, J = 17.7 Hz), 6.65 (dd, 1H, J = 17.7, 11.1 Hz), 6.95 (s, 1H), 7.20 (br-s, 1H), 7.35-7.53 (m, 5H), 7.88 (s, 1H). 1-76 1.22 (t, 3H, J = 7.0 Hz), 1.51 (s, 9H), 3.58 (q, 2H, J = 7.0 Hz), 3.78 (t, 2H, J = 4.7 Hz), 3.98 (s, 3H), 4.18 (t, 2H, J = 4.7 Hz), 5.17 (s, 2H), 6.52 (d, 1H, J = 2.2 Hz), 7.25 (br-s, 1H), 7.34-7.53 (m, 6H). 1-77 1.31 (d, 6H, J = 7.8 Hz), 1.51 (s, 9H), 3.98 (s, 3H), 4.66 (hept, 1H, J = 7.8 Hz), 5.17 (s, 2H), 6.42 (d, 1H, J = 1.8 Hz), 7.22 (br-s, 1H), 7.34-7.53 (m, 6H). 1-78 0.96 (t, 3H, J = 7.2 Hz), 1.41-1.48 (m, 2H), 1.52 (s, 9H), 1.71-1.80 (m, 2H), 3.98 (s, 3H), 4.03 (t, 2H, J = 6.6 Hz), 5.19 (s, 2H), 6.47 (d, 1H, J = 1.8 Hz), 7.34-7.62 (m, 7H). 1-82 1.51 (s, 9H), 3.00 (s, 6H), 3.98 (s, 3H), 5.16 (s, 2H), 6.15 (d, 1H), 7.02 (brs, 1H), 7.11 (d, 1H), 7.37-7.44 (m, 3H), 7.52-7.55 (m, 2H) 1-83 1.49 (s, 9H), 1.52 (s, 9H), 3.30 (s, 3H), 4.01 (s, 3H), 5.21 (s, 2H), 7.12 (d, 1H, J = 1.9 Hz), 7.14 (br-s, 1H), 7.35-7.55 (m, 5H), 7.80 (d, 1H, J = 1.9 Hz). 1-86 1.51 (s, 9H), 3.31 (t, 4H, J = 4.9 Hz), 3.81 (t, 4H, J = 4.9 Hz), 3.99 (s, 3H), 5.17 (s, 2H), 6.30 (d, 1H, J = 2.2 Hz), 7.16 (br-s, 1H), 7.32-7.65 (m, 6H). 1-89 1.53 (s, 9H), 3.87 (s, 3H), 4.03 (s, 3H), 5.70 (s, 2H), 7.34-7.55 (m, 5H), 7.77 (br-s, 1H), 7.93 (d, 1H), 8.21 (d, 1H). 1-90 1.54 (s, 9H), 3.99 (s, 3H), 5.28 (s, 2H), 7.15 (s, 1H), 7.35-7.51 (m, 6H), 8.18 (s, 1H). 1-131 0.95 (t, 3H, J = 7.3 Hz), 1.37-1.44 (m, 2H), 1.60-1.70 (m, 2H), 3.99 (s, 3H), 4.16 (t, 2H, J = 6.7 Hz), 4.25 (br- s, 2H), 5.14 (s, 2H), 6.18 (d, 1H, J = 2.0 Hz), 7.16 (d, 1H, J = 2.0 Hz), 7.35-7.47 (m, 3H), 7.51-7.54 (m, 2H) 1-132 0.95 (t, 3H, J = 7.4 Hz), 1.41 (tq, 2H, J = 7.6, 7.4 Hz), 1.51 or 1.55 (s, 9H), 1.66 (tt, 2H, J = 7.6, 6.7 Hz), 4.03 (s, 3H), 4.18 (t, 2H, J = 6.7 Hz), 5.20 (s, 2H), 6.72 (br-s, 1H), 7.20 (br-s, 1H), 7.35-7.54 (m, 5H), 7.78 (d, 1H, J = 1.8 Hz) 1-197 1.23 (t, 3H), 1.24 (d, 6H), 2.90 (septet, 1H), 3.55 (q, 2H), 3.69 (t, 2H), 3.99 (s, 3H), 4.34 (t, 2H), 5.23 (s, 2H), 6.82 (s, 1H), 7.35-7.54 (m, 6H), 7.79 (s, 1H). 1-275 1.52 (s, 9H), 3.99 (s, 3H), 5.20 (s, 2H), 6.94 (d, 1H, J = 1.6 Hz), 7.20 (br-s, 1H), 7.35-7.52 (m, 5H), 7.96 (d, 1H, J = 1.5 Hz) 1-278 1.53 (s, 9H), 3.99 (s, 3H), 5.19 (s, 2H), 7.09 (s, 1H), 7.15 (br-s, 1H), 7.36-7.51 (m, 5H), 8.13 (s, 1H) 1-377 4.00 (s, 3H), 5.31 (s, 2H), 7.15 (d, 1H), 7.36-7.51 (m, 6H), 7.80 (dd, 1H), 8.12 (d, 1H), 8.65 (br-s, 1H). 1-398 in CD₃OD 1.34-1.70 (m, 6H), 2.37 (t, 2H), 2.84 (t, 2H), 3.92 (s, 3H), 4.59 (br-s, 2H), 5.21 (s, 2H), 7.02 (d, 1H), 7.29-7.67 (m, 6H), 7.70 (t, 1H), 7.93 (d, 1H) 1-399 2.13 (br-s, 1H), 3.45 (s, 2H), 3.87 (s, 2H), 3.97 (s, 3H), 5.30 (s, 2H), 7.02 (d, 1H), 7.23-7.54 (m, 10H), 7.70 (t, 1H), 8.17 (d, 1H), 9.69 (br-s, 1H) 1-400 1.47 (s, 9H), 3.98 (s, 3H), 4.52 (d, 2H), 4.58 (s, 2H), 5.27 (s, 2H), 7.02 (d, 1H), 7.26-7.52 (m, 11H), 7.71 (t, 1H), 8.14 (d, 1H) 1-405 3.95 (s, 3H), 4.64 (s, 3H), 5.30 (s, 3H), 7.01 (d, 1H), 7.02-7.08 (m, 2H), 7.32-7.53 (m, 8H), 7.74 (t, 1H), 8.22 (d, 1H), 8.87 (br-s, 1H). 1-411 4.03 (s, 3H), 4.75 (s, 2H), 5.31 (s, 2H), 7.01 (d, 1H), 7.07 (d, 1H), 7.16 (t, 1H), 7.37-7.67 (m, 7H), 7.34 (t, 1H), 8.17 (d, 1H), 8.86 (s, 1H). 1-415 3.99 (s, 3H), 4.58 (q, 2H, JC-F = 8.3 Hz), 5.72 (s, 2H), 7.01 (d, 1H, J = 7.7 Hz), 7.35-7.52 (m, 6H), 7.72 (dd, 1H, J = 8.1, 7.7 Hz), 7.86 (d, 1H, J = 8.1 Hz). 1-418 1.76 (s, 6H), 3.98 (s, 3H), 5.26 (s, 2H), 6.97 (d, 1H), 7.34-7.52 (m, 6H), 7.68 (t, 1H), 7.80 (d, 1H) 1-420 3.99 (s, 3H), 4.66 (t, 2H), 5.27 (s, 2H), 7.01 (d, 1H), 7.33-3.54 (m, 6H), 7.73 (dd, 1H), 7.86 (d, 1H). 1-421 3.98 (s, 3H), 4.69 (d, 2H, J = 5.7 Hz), 5.26 (s, 2H), 5.27 (d, 1H, J = 10.8 Hz), 5.37 (d, 1H, J = 17.3 Hz), 5.97 (ddt, 1H, 17.3, 10.8, 5.7 Hz), 6.96 (d, 1H, J = 7.5 Hz), 7.31-7.52 (m, 6H), 7.68 (dd, 1H, J = 8.2, 7.5 Hz), 7.89 (d, 1H, 8.2 Hz). 1-422 1.75 (s, 3H), 1.78 (s, 3H), 3.98 (s, 3H), 4.68 (d, 2H, J = 7.4 Hz), 5.25 (s, 2H), 5.40 (tdd, 1H, J = 7.4, 1.4, 1.3 Hz), 6.95 (d, 1H, J = 7.6 Hz), 7.24 (br, 1H), 7.34-7.53 (m, 5H), 7.67 (dd, 1H, J = 8.4, 7.6 Hz), 7.90 (d, 1H, 8.4 Hz). 1-423 1.59 (s, 6H), 3.97 (s, 3H), 5.13 (d, 1H), 5.23 (d, 1H), 5.25 (s, 2H), 6.15 (dd, 1H), 6.93 (d, 1H), 7.34-7.52 (m, 6H), 7.64 (t, 1H), 7.86 (d, 1H) 1-424 1.33 (d, 3H), 1.74 (d, 6H), 3.97 (s, 3H), 5.18-5.31 (m, 1H), 5.24 (s, 2H), 5.58-5.63 (m, 1H), 6.93 (d, 1H), 7.19 (br-s, 1H), 7.35-7.55 (m, 5H), 7.66 (t, 1H), 7.89 (d, 1H) 1-428 1.75 (s, 6H), 2.59 (s, 1H), 3.97 (s, 3H), 5.25 (s, 2H), 6.95 (d, 1H), 7.34-7.52 (m, 6H), 7.64 (t, 1H), 7.93 (d, 1H). 1-430 1.71 (s, 6H), 1.86 (s, 3H), 3.97 (s, 3H), 5.25 (s, 2H), 6.94 (d, 1H), 7.34-7.52 (m, 6H), 7.66 (t, 1H), 7.92 (d, 1H) 1-431 1.13 (t, 3H), 1.72 (s, 6H), 2.23 (q, 2H), 4.00 (s, 3H), 5.24 (s, 2H), 6.93 (d, 1H), 7.21 (br-s, 1H), 7.34 (m, 5H), 7.66 (t, 1H), 7.92 (d, 1H) 1-435 1.84 (s, 6H), 3.97 (s, 3H), 5.25 (s, 2H), 6.94 (d, 1H, J = 7.8 Hz), 7.24-7.52 (m, 11H), 7.66 (dd, 1H, J = 8.1, 7.8 Hz), 7.92 (d, 1H, J = 8.1 Hz). 1-437 1.15 (t, 3H), 2.22 (q, 2H), 3.59 (q, 2H), 3.98 (s, 3H), 4.30 (t, 2H), 5.26 (s, 2H), 5.96 (br-s, 1H), 6.98 (d, 1H), 7.35-7.52 (m, 6H), 7.69 (t, 1H), 7.87 (d, 1H). 1-443 1.10 (s, 6H), 2.32 (s, 6H), 3.98 (s, 3H), 4.10 (s, 2H), 5.25 (s, 2H), 6.95 (d, 1H), 7.34-7.53 (m, 6H), 7.68 (t, 1H), 7.89 (d, 1H) 1-444 1.30 (d, 3H), 2.29 (s, 6H), 2.60 (dd, 1H), 3.98 (s, 3H), 5.05 (tq, 1H), 5.25 (s, 2H), 6.94 (d, 1H), 7.34-7.52 (m, 6H), 7.66 (t, 1H), 7.88 (d, 1H) 1-445 0.30-0.35 (m, 2H), 0.57-0.63 (m, 2H), 1.14-1.24 (m, 1H), 3.98 (s, 3H), 4.02 (d, 2H, J = 7.3 Hz), 5.26 (s, 2H), 6.96 (d, 1H, J = 7.1 Hz), 7.28 (br, 1H), 7.35-7.53 (m, 5H), 7.68 (dd, 1H, J = 8.2, 7.1 Hz), 7.89 (d, 1H, J = 8.2 Hz). 1-446 0.27-0.32 (m, 1H), 0.43-0.59 (m, 3H), 1.01-1.04 (m, 1H), 1.36 (d, 3H), 3.98 (s, 3H), 4.33 (q, 1H), 5.26 (s, 2H), 6.94 (d, 1H), 7.32-7.52 (m, 6H), 7.67 (t, 1H), 7.88 (d, 1H) 1-448 1.30 (d, 3H), 2.82 (dd, 1H), 2.30 (dd, 1H), 3.97 (s, 3H), 5.13 (q, 1H), 5.25 (s, 2H), 6.94 (d, 1H), 7.21-7.52 (m, 11H), 7.66 (t, 1H), 7.86 (d, 1H) 1-449 1.61 (d, 3H), 3.97 (s, 3H), 5.24 (s, 2H), 5.89 (q, 1H), 6.94 (d, 1H), 7.31-7.52 (m, 11H), 7.65 (t, 1H), 7.87 (d, 1H) 1-450 2.04 (s, 6H), 3.97 (s, 3H), 5.25 (s, 2H), 6.91 (d, 1H), 7.23-7.52 (m, 11H), 7.58 (t, 1H), 7.77 (d, 1H) 1-451 3.97 (s, 3H), 5.25 (s, 2H), 5.27 (s, 2H), 6.97 (d, 1H), 7.34-7.71 (m, 11H), 7.88 (d, 1H) 1-456 3.81 (s, 3H), 3.97 (s, 3H), 5.19 (s, 2H), 5.24 (s, 2H), 6.86-6.98 (m, 4H), 7.35-7.52 (m, 7H), 7.68 (m, 1H), 7.90 (d, 1H, J = 8.1 Hz). 1-457 3.86 (s, 3H), 3.97 (s, 3H), 5.24 (s, 2H), 5.28 (s, 2H), 6.89-6.98 (m, 3H), 7.30-7.52 (m, 8H), 7.67 (m, 1H), 7.92 (d, 1H, J = 8.4 Hz). 1-465 3.81 (s, 3H), 3.96 (s, 3H), 5.15 (s, 2H), 5.24 (s, 2H), 6.90 (m, 2H), 6.94 (d, 1H, J = 7.2 Hz), 7.32-7.51 (m, 8H), 7.67 (m, 1H), 7.90 (d, 2H, J = 8.1 Hz). 1-466 3.97 (s, 3H), 5.11 (s, 2H), 5.24 (s, 2H), 5.97 (s, 2H), 6.78-6.96 (m, 4H), 7.34-7.52 (m, 6H), 7.68 (t, 1H), 7.90 (d, 1H) 1-467 3.98 (s, 3H), 5.26 (s, 2H), 5.34 (s, 2H), 6.97 (d, 1H), 7.23-7.75 (m, 10H), 7.91 (d, 1H), 8.61 (d, 1H) 1-470 3.98 (s, 3H), 5.26 (s, 2H), 5.52 (s, 2H), 6.99 (d, 1H), 7.34-7.52 (m, 7H), 7.70 (t, 1H), 7.82 (br-s, 1H), 7.92 (d, 1H) 1-471 3.99 (s, 3H), 5.27 (s, 2H), 5.61 (s, 2H), 6.99 (d, 1H), 7.34-7.68 (m, 9H), 7.74 (dd, 1H), 7.91-7.93 (m, 1H), 8.05 (d, 1H). 1-474 1.60 (d, 3H), 3.98 (s, 3H), 5.26 (s, 2H), 6.97 (d, 1H), 7.28-7.51 (m, 8H), 7.67 (t, 1H), 7.84 (d, 1H), 8.60 (d, 2H) 1-477 1.19 (d, 6H, J = 5.9 Hz), 3.59-3.69 (m, 3H), 3.98 (s, 3H), 4.32 (t, 2H, J = 4.8 Hz), 5.26 (s, 2H), 6.96 (d, 1H, J = 7.6 Hz), 7.34-7.53 (m, 6H), 7.68 (dd, 1H, J = 8.1, 7.6 Hz), 7.89 (d, 1H, J = 8.1 Hz). 1-480 1.52 (s, 6H), 3.41 (s, 3H), 3.56 (s, 2H), 3.97 (s, 3H), 5.25 (s, 2H), 6.93 (d, 1H), 7.35-7.53 (m, 6H), 7.65 (t, 1H), 7.85 (d, 1H). 1-481 1.31 (d, 3H), 3.39 (s, 3H), 3.47 (d, 2H), 3.98 (s, 3H), 5.09 (tq, 1H), 5.25 (s, 2H), 6.95 (d, 1H), 7.34-7.52 (m, 6H), 7.67 (t, 1H), 7.89 (d, 1H) 1-482 3.98 (s, 3H), 4.19 (t, 2H, J = 4.7 Hz), 4.53 (t, 2H, J = 4.7 Hz), 5.25 (s, 2H), 6.85 (d, 2H, J = 9.0 Hz), 6.97 (d, 1H, J = 7.5 Hz), 7.24 (d, 2H, J = 9.0 Hz), 7.34-7.52 (m, 6H), 7.69 (dd, 1H, J = 8.6, 7.5 Hz), 7.88 (d, 1H, 8.6 Hz). 1-486 3.73 (t, 2H, J = 4.8 Hz), 3.98 (s, 3H), 4.37 (t, 2H, J = 4.8 Hz), 4.58 (s, 2H), 5.25 (s, 2H), 6.96 (d, 1H, J = 7.5 Hz), 7.29-7.53 (m, 11H), 7.68 (dd, 1H, J = 8.6, 7.5 Hz), 7.88 (d, 1H, J = 8.6 Hz). 1-488 1.65-1.85 (m, 4H), 2.11 (s, 3H), 2.54 (t, 2H, J = 7.0 Hz), 3.98 (s, 3H), 4.21 (t, 2H, J = 6.3 Hz), 5.26 (s, 2H), 6.96 (d, 1H, J = 7.5 Hz), 7.28 (s, 1H), 7.34-7.53 (m, 5H), 7.68 (dd, 1H, J = 8.2, 7.5 Hz), 7.89 (d, 1H, J = 8.2 Hz). 1-491 1.82-1.98 (m, 4H), 2.59 (s, 3H), 2.67-2.83 (m, 2H), 3.98 (s, 3H), 4.24 (t, 2H, J = 5.8 Hz), 5.26 (s, 2H), 6.96 (d, 1H, J = 7.5 Hz), 7.35-7.53 (m, 6H), 7.69 (dd, 1H, J = 8.4, 7.5 Hz), 7.88 (d, 1H, J = 8.4 Hz). 2-68 1.53 (s, 6H), 2.42 (s, 3H), 3.89 (s, 3H), 5.18 (s, 2H), 7.33-7.51 (m, 5H), 8.26 (br-s, 1H) 2-82 1.55 (s, 9H), 3.97 (s, 3H), 5.32 (s, 2H), 7.35-7.52 (m, 5H), 8.69 (brs, 1H). 2-94 1.55 (s, 9H), 3.89 (s, 3H), 5.29 (s, 2H), 7.33-7.49 (m, 10H), 8.67 (br-s, 1H). 2-399 2.00 (tt, 2H), 2.16 (s, 3H), 2.49 (t, 2H), 2.59 (t, 2H), 3.95 (s, 3H), 5.25 (s, 2H), 6.91 (s, 1H), 7.34-7.52 (m, 5H), 9.25 (br-s, 1H)

Each of the tetrazoyloxime derivatives represented by formula (1) or salts thereof (hereinafter referred to as the “compound of the present invention”) has excellent fungicidal activity against wide range of fungi belonging to, for example, Oomycetes, Ascomycetes, Deuteromycetes and Basidiomycetes. Therefore, the composition containing the compound of the present invention as the active ingredient can be used for controlling various plant diseases infesting on agricultural and horticultural crops including ornamental flowers, lawns and forage crops by means of seed treatment, foliage application, soil application, or water surface application.

For example, it is possible to use the composition containing the compound of the present invention for controlling plant diseases shown below.

Sugar beet: Cercospora leaf spot (Cercospora beticola)

-   -   Aphanomyces root rot (Aphanomyces cochlioides)         Peanut: Brown leaf spot (Mycosphaerella arachidis)     -   Leaf spot (Mycosphaerella berkeleyi)         Cucumber: Powdery mildew (Sphaerotheca fuliginea)     -   Gummy stem blight (Mycosphaerella melonis)     -   Stem rot (Sclerotinia sclerotiorum)     -   Gray mold (Botrytis cinerea)     -   Scab (Cladosporium cucumerinum)     -   Downy mildew (Pseudoperonospora cubensis)         Tomato: Gray mold (Botrytis cinerea)     -   Leaf mold (Cladosporium fulvum)     -   Cottony leak (Phythium aphanidermatum)     -   Late blight (Phytophthora infestans)         Eggplant: Gray mold (Botrytis cinerea)     -   Black rot (Corynespora melongeneae)     -   Powdery mildew (Erysiphe cichoracearum)         Spinach Damping-off (Pythium ultimum)

Strawberry:

-   -   Gray mold (Botrytis cinerea)     -   Powdery mildew (Sphaerotheca aphanis)         Onion: Gray-mold neck rot (Botrytis allii)     -   Gray-mold (Botrytis cinerea),         Kidney bean:     -   Stem rot (Sclerotinia sclerotiorum)     -   Gray mold (Botrytis cinerea)         Apple: Powdery mildew (Podosphaera leucotricha)     -   Scab (Venturia inaequalis)     -   Blossom blight (Monilinia mali)

Persimon:

-   -   Powdery mildew (Phyllactinia kakicola)     -   Anthracnose (Gloeosporium kaki)     -   Angular leaf spot (Cercospora kaki)

Peach & Cherry:

-   -   Brown rot (Monilinia fructicola)     -   Grape: Gray mold (Botrytis cinerea)     -   Powdery mildew (Uncinula necator)     -   Ripe rot (Glomerella cingulata)     -   Downy mildew (Plasmopara viticola)         Pear: Scab (Venturia nashicola)     -   Rust (Gymnosporangium asiaticum)     -   Black spot (Alternaria kikuchiana)         Tea: Gray blight (Pestalotia theae)     -   Anthracnose (Colletotrichum theae-sinensis)         Citrus: Scab (Elsinoe fawcetti)     -   Blue mold (Penicillium italicum)     -   Common green mold (Penicillium digitatum)     -   Gray mold (Botrytis cinerea)         Barley: Powdery mildew (Erysiphe graminis f.sp. hordei)     -   Loose smut (Ustilago nuda)         Wheat: Scab (Gibberella zeae)     -   Leaf rust (Puccinia recondita)     -   Spot blotch (Cochliobolus sativus)         -   Glume blotch (Leptosohaeria nodorum)     -   Eye spot (Pseudocercosporella herpotrichoides)     -   Powdery mildew (Erysiphe graminis f.sp. tritici)     -   Snow mold (Micronectriella nivalis)     -   Browning root rot (Pythium iwayamai)

Rice:

-   -   Blast (Pyricularia oryzae)     -   Sheath blight (Rhizoctonia solani)     -   Bakanae disease (Gibberella fujikuroi)     -   Brown spot (Cochliobolus miyabeanus)     -   Seeding blight (Pythiym graminicolum)         Soybean: Purple speck of seed (Cercospora kikuchii)     -   Downy mildew (Peronospora manshurica)     -   Phytophthora root rot (Phytophthora sojae)         Potato: Late blight (Phytophthora infestans)         Cruciferous plants:     -   Clubroot(Plasmodiophora brassicae)         Tobacco: Stem rot (Sclerotinia sclerotiorum)     -   Powdery mildew (Erysiphe cichoracearum)         Tulip: Gray mold (Botrytis cinerea)         Bent grass: Sclerotinia snow blight (Sclerotinia borealis)     -   Pythium red blight (Pythium aphanidermatum)         Orchard grass:     -   Powdery mildew (Erysiphe graminis)

Besides, in recent years, various plant pathogenic fungi have developed resistance to phenylamide fungicides and strobilurin fungicides. It follows that there is a problem in the control of such a problematic plant disease, because no fungicide can control those plant diseases sufficiently. Therefore, an effective fungicide, which can control such fungi being resistant against those problematic plant diseases is desired. The compounds of the present invention are effective to those resistant strains of fungi to aforementioned fungicides as well as susceptible ones.

For example, the compounds of the present invention are also effective to those resistant strains of fungi to Late blight of potato and tomato (Phytophthora infestans), Downy mildew of cucumber (Pseudoperonospora cubensis) and Downy mildew of grape (Plasmopara viticola) which show resistance to metalaxyl, as well as susceptible ones.

Furthermore, the compounds of the present invention are also effective to Downy mildew of cucumber (Pseudoperonospora cubensis) and Downy mildew of grape (Plasmopara viticola) which show resistance to strobilurin fungicides (for example, kresoxim-methyl, azoxystrobin, etc.) similar to susceptible fungi.

Examples of preferred plant injury to which the compounds of the present invention are applied include various plant injuries caused by Oomycetes such as Downy mildew of grape (Plasmopara viticola), Downy mildew of gourds (Pseudoperonospora cubensis), Late blight of potato and tomato (Phytophthora infestans), Pythium disease of the grass (Pythium aphanidermatum, etc.) and Black root of sugar beet (Aphanomyces cochlioides).

Further, the compounds of the present invention can be used also as an antifouling agent which prevents water-dwelling organisms from adhering to structures placed in water such as the outer bottom of a vessel and fishing net.

Moreover, the intermediate chemical compounds of the chemical compounds of the present invention may have fungicidal activities.

Also, the compounds of the present invention can be contained in paints and fibers and thereby used as an antimicrobial and antifungal agent for walls, bathtubs, shoes and clothes.

2) Plant Disease Controlling Agent

The second aspect of the present invention is directed to a plant disease controlling agent containing the compound of the present invention as an active ingredient.

The plant disease controlling agent of the present invention can be used in the state of the compounds of the present invention alone without the addition of other ingredients or, for the use as agricultural chemicals, the compound can be applied in forms of general formulations for agricultural chemicals, such as wettable powders, granules, powders, emulsifiable concentrates, aqueous solutions, suspensions and flowables.

For the additives and carriers to be used in the plant disease controlling agent of the present invention, vegetable powders such as soybean powder and wheat powder, mineral fine powders such as diatomaceous earth, apatite, gypsum, talc, bentonite, pyrophyllite and clay, and organic and inorganic compounds such as sodium benzoate, urea and salt cake can be used, when the compounds are formulated into solid formulations.

When the compounds are formulated into liquid formulations, petroleum fractions such as kerosine, xylene and solvent naphtha, cyclohexane, cyclohexanone, dimethylformamide, dimethylsulfoxide, alcohol, acetone, trichloroethylene, methylisobutylketone, mineral oil, vegetable oil and water, can be used as the solvent.

In the plant disease controlling agent of the present invention, surfactants may be added to the formulations in order to make the formulations homogeneous and stable, if appropriate.

Examples of the surfactants include nonionic surfactants such as alkyl phenyl ether added with polyoxyethylene, alkyl ether added with polyoxyethylene, higher fatty acid ester added with polyoxyethylene, sorbitan higher fatty acid ester added with polyoxyethylene, tristyrylphenyl ether added with polyoxyethylene; sulfuric ester salt of alkyl phenyl ether added with polyoxyethylene, alkylbenzene sulfonate salt, sulfuric ester salt of higher alcohol, alkylnaphthalene sulfonate salt, polycarboxylate salt, lignin sulfonate salt, formaldehyde condensate of alkylnaphthalene sulfonate, and copolymer of isobutylene-maleic anhydride.

In general, the content of an active ingredient in the formulations is within a range from 0.5 to 95% by weight, and preferably from 2 to 70% by weight, based on the total weight of the composition (formulation).

When the plant disease controlling agent of the present invention is in the form of wettable powders, emulsifiable concentrates and flowable formulations, it can be applied in a form prepared by diluting the formulations with water to the suspension or the emulsion at a desired concentrations, while the powders and the granules of the said compound can be directly dispersed to plants.

Needless to say that the compound of the present invention or the plant disease controlling agent of the present invention alone has sufficient fungicidal activity, however, it can be used in combination with one kind, two kinds, or more of various types of fungicides, insecticides, acaricides and synergists.

Typical examples for the fungicides, insecticides, acaricides and plant growth regulators, those which are usable in admixing with the compounds of the present invention or the plant disease controlling agent of the present invention, are shown below.

Fungicides:

Copper agents: basic copper chloride, basic copper sulfate

Sulfur agents: thiuram, zineb, maneb, mancozeb, ziram, propineb, polycarbamate, etc.

Polyhaloalkylthio agents: captan, folpet, dichlorofluanid, etc.

Organic chlorine agents: chlorothalonil, phthalate, etc.

Organic phosphorous agents: IBP, EDDP, trichlophosmethyl, pyrazophos, fosetyl, etc.

Benzimidazole agents: thiophanate-methyl, benomyl, carbendazim, thiabendazole, etc.

Dicarboxyimide agents: iprodione, procymidone, vinclozolin, fluoroimide, etc.

Carboxyamide agents: oxycarboxin, mepronil, flutolanil, tecloftalam, trichlamide, pencycuron, etc.

Acylalanine agents: metalaxyl, oxadixyl, furalaxyl, etc.

Strobilurin-based agents: azoxystrobin, kresoxim-methyl, pyraclostrobin, trifloxystrobin, pyribencarb, famoxadone, fenamidone, etc.

Anilinopyrimidine agents: andoprin, mepanipyrim, pyrimethanil, diprozinil, etc.

SBI agents: triadimefon, triadimenol, bitertanol, myclobutanil, hexaconazole, propiconazole, triflumizole, prochloraz, pefurazoate, fenarimol, pyrifenox, triforine, flusilazole, etaconazole, dichlobutrazol, fluotrimazole, flutriafen, penconazole, diniconazole, imazalil, tridemorph, fenpropimorph, buthiobate, epoxiconazole, metconazole, prothioconazole, spiroxamine, fenhexamid, pyributycarb, etc.

Antibiotic agents: polyoxins, blasticidin-S, kasugamycin, validamycin, dihydrostreptomycin sulfate, etc.

Anilide-based agents: boscalid, penthiopyrad, fluopyram, bixafen, etc.

Guanidine-based agents: iminoctadine acetate salt, iminoctadine albesilate salt, dodine, guazatine, etc.

Valine-based agents: dimethomorph, flumorph, iprovalicarb, benthiavalicarb, mandipropamid, etc.

Others: cymoxanil, cyazofamid, amisulbrom, propamocarb, fluazinam, propamocarb acetate salt, ethaboxam, fluopicolide, zoxamide, cyflufenamid, metrafenone, proquinazid, hydroxy isoxazole, metasulfocarb, anilazine, isoprothiolane, ferimzone, probenazole, tiadinil, acibenzolar s-methyl, isotianil, pyroquilon, phthalide, tricyclazole, carpropamid, fenoxanil, diclocymet, fluazinam, fludioxonil, pyrrolenitrine, hydroxyl isoxazole, flusulfamide, diethofencarb, quintozene, metasulfocarb, anilazine, quinomethionate, dithianon, dinocap, dichlomezine, oxolinic acid, lecithin, sodium bicarbonate, fenaminosulf, phenazine oxide, etc.

Insecticides/Acaricides:

Organic phosphorous and carbamate-based insecticides: fenthion, fenitrothion, diazinon, chlorpyrifos, ESP, vamidothion, phenthoate, dimethoate, formothion, malathion, trichlorfon, thiometon, phosmet, dichlorvos, acephate, EPBP, methyl parathion, oxydemeton-methyl, ethion, salithion, cyanophos, isoxathion, pyridafenthion, phosalone, methidathion, sulprofos, chlorfenvinphos, tetrachlorvinphos, dimethylvinphos, propaphos, isofenphos, ethylthiometon, profenofos, pyraclofos, monocrotophos, azinphos-methyl, aldicarb, methomyl, thiodicarb, carbofuran, carbosulfan, benfuracarb, furathiocarb, propoxur, BPMC, MTMC, MIPC, carbaryl, pirimicarb, ethiophencarb, fenoxycarb, etc.

Pyrethroid-based insecticides: permethrin, cypermethrin, deltamethrin, fenvalerate, fenpropathrin, pyrethrins, allethrin, tetramethrin, resmethrin, dimethrin, propathrin, phenothrin, prothrin, fluvalinate, cyfluthrin, cyhalothrin, flucythrinate, etofenprox, cycloprothrin, tralomethrin, silafluofen, Halfenprox, acrinathrin, etc.

Benzoylurea-based and other insecticides: diflubenzuron, chlorfluazuron, hexaflumuron, triflumuron, tetrabenzuron, flufenoxuron, flucycloxuron, buprofezin, pyriproxyfen, methoprene, benzoepin, diafenthiuron, acetamiprid, imidacloprid, nitenpyram, fipronil, cartap, thiocyclam, bensultap, nicotine sulfate, rotenone, metaldehyde, emamectin, flubendiamide, spinosad, machine oil, BT, insect pathogen viruses and other microbial agricultural chemicals, etc.

Nematicides: phenamiphos, fosthiazate, etc.

Acaricides: chlorobenzilate, phenisobromolate, dicofol, amitraz, BPPS, benzomate, hexathiazox, fenbutatin oxide, polynactin, quinomethionate, CPCBS, tetradifon, abamectin, milbemectin, clofentezine, cyhexatin, pyridaben, fenpyroximate, tebufenpyrad, pyrimidifen, fenothiocarb, dienochlor, fluacrypyrim, etc.

Plant Growth Regulators: gibberellins (e.g., gibberellin A3, gibberellin A4, gibberellin A7, etc.), IAA, NAA, etc.

EXAMPLES

The present invention will be explained in more detail by way of Examples, but the present invention should not be interpreted to be limited to these Examples.

Preparation Example Step 1

A mixture of 2.94 g (11.4 mmol) of diethyl 4-chloro-2,6-pyridine dicarboxylate and 20 mL of ethanol was heated to 55° C. and an aqueous solution prepared from 0.27 g (6.8 mmol) of sodium hydroxide and 50 mL of water was added dropwise to the mixture for 8 hours. After completion of the dropwise addition, the mixed solution was stirred for one hour and allowed to stand overnight at room temperature. After the solvent was removed under reduced pressure, the residue was back-extracted with water/ethyl acetate. The organic layer was washed with water and the aqueous layers were combined. Then concentrated hydrochloric acid was added to the aqueous layer thereby adjusting the pH to 2.5. The aqueous layer was extracted with ethyl acetate, washed with saturated brine and then dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to obtain 1.42 g (6.2 mmol, yield of 54%) of monoethyl 4-chloro-2,6-pyridine dicarboxylate.

Step 2

To a mixture of 1.42 g (6.2 mmol) of monoethyl 4-chloro-2,6-pyridine dicarboxylate, 12 mL of anhydrous tetrahydrofuran and 0.69 g (6.8 mmol) of triethylamine, 1.87 g (6.8 mmol) of diphenyl phosphoryl azide was added at room temperature, followed by heating to 60° C. and further stirring for one hour.

To the reaction mixture, 0.93 g (12.6 mmol) of t-butanol was added, followed by further stirring at 60° C. for 18 hours. The reaction solution was added to water, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=5/1 (v/v)) to obtain 1.00 g (3.3 mmol, yield of 54%) of ethyl 2-(t-butoxycarbonyl)amino-4-chloropicolinate.

Step 3

To a mixture of 1.00 g (3.3 mmol) of ethyl 2-(t-butoxycarbonyl)amino-4-chloropicolinate and 20 mL of anhydrous ethanol, 0.38 g (10.0 mmol) of sodium borohydride was added, followed by stirring at room temperature for 17 hours. To the reaction solution, dilute hydrochloric acid was added thereby adjusting the pH to 2 and the solution was neutralized by adding saturated sodium bicarbonate aqueous solution. After ethanol was removed under reduced pressure, the resultant was extracted with ethyl acetate and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure and the resultant residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=3/1 (v/v)) to obtain 0.75 g (2.9 mmol, yield of 87%) of 2-(t-butoxycarbonyl)amino-4-chloro-6-hydroxymethylpyridine.

To a mixture of 0.74 g (2.9 mmol) of 2-(t-butoxycarbonyl)amino-4-chloro-6-hydroxymethylpyridine and 20 mL of dichloromethane 20 mL, 0.29 g (3.7 mmol) of pyridine was added, and 0.41 g (3.5 mmol) of thionyl chloride was further added, followed by stirring at room temperature for 3.5 hours. The reaction solution was added to water and saturated sodium bicarbonate aqueous solution was added thereby adjusting the pH to 6, followed by extraction with chloroform. The organic layer was dried over anhydrous magnesium sulfate and the solvent was removed under reduced pressure. The resultant residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=9/1 (v/v)) to obtain 0.56 g (2.0 mmol, yield of 71%) of 2-(t-butoxycarbonyl)amino-4-chloro-6-chloromethylpyridine.

Step 5

A mixture of 5 mL of dry N,N-dimethylformamide and 0.12 g (0.6 mmol) of (Z)-(1-methyl-1H-tetrazol-5-yl)phenylmethanone oxime was cooled in an ice bath and 0.03 g (60% in oil, 0.75 mmol) of sodium hydride was added to the solution. After the suspension was stirred for 5 minutes, a mixture of 0.19 g (0.69 mmol) of 2-(t-butoxycarbonyl)amino-4-chloro-6-chloromethylpyridine and 5 mL of N,N-dimethylformamide was added, followed by stirring at room temperature for 3 hours.

The reaction mixture was added to an aqueous saturated ammonium chloride solution and then extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and the solvent was removed under reduced pressure. The resultant residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=4/1 (v/v)) to obtain 0.16 g (0.3 mmol, yield of 62%) of (Z)-(1-methyl-1H-tetrazol-5-yl)phenylmethanone-O-[2-(t-butoxycarbonyl)amino-4-chloropyridin-6-ylmethyl]-oxime (compound of a compound number 1-275 in Table 1)

Although several Formulation Examples of the plant disease controlling agent of the present invention are shown below, additives and the additive ratio should not be limited thereto and can be broadly changed. Parts shown in the Formulation Examples are by weight.

Formulation Example 1 Wettable Powders

Compound of the present invention 40 parts Clay 53 parts Sodium dioctyl sulfosuccinate  4 parts Sodium lignin sulfonate  3 parts

The above components are uniformly mixed and finely ground to obtain wettable powders containing 40% of an active ingredient.

Formulation Example 2 Emulsifiable Concentrates

Compound of the present invention 10 parts Sorbesso 200 53 parts Cyclohexanone 26 parts Calcium dodecylbenzene sulfonate 1 part Polyoxyethylene alkyl allyl ether 10 parts

The above components are mixed and dissolved to obtain emulsifiable concentrates containing 10% of an active ingredient.

Formulation Example 3 Powders

Compound of the present invention 10 parts Clay 90 parts

The above components are uniformly mixed and finely ground to obtain powders containing 10% of an active ingredient.

Formulation Example 4 Granules

Compound of the present invention 5 parts Clay 73 parts Bentonite 20 parts Sodium dioctyl sulfosuccinate 1 part Potassium phosphate 1 part

The above components are well ground and mixed, well kneaded with water, granulated and then dried to obtain granules containing 5% of an active ingredient.

Formulation Example 5 Suspensions

Compound of the present invention 10 parts Polyoxyethylene alkyl allyl ether 4 parts Sodium polycarboxylate 2 parts Glycerin 10 parts Xanthan gum 0.2 part Water 73.8 parts

The above components are mixed, and ground by wet grinding to a particle size of 3 micron or less to obtain suspensions containing 10% of an active ingredient.

Formulation Example 6 Granular Wettable Powders

Compound of the present invention 40 parts Clay 36 parts Potassium chloride 10 parts Sodium alkylbenzene sulfonate 1 part Sodium lignin sulfonate 8 parts Formaldehyde condensate of sodium alkylbenzene 5 parts sulfonate

The above components are uniformly mixed and finely ground and then kneaded with an appropriate amount of water to form a clay-like substance. The clay-like substance is granulated and then dried to obtain granular wettable powders containing 40% of an active ingredient.

Test Example Tomato Late Blight Control Test

An emulsifiable concentrate of Formulation Example 2 was sprayed over the tomato seedling (cultivar: “Regina”, 4-5 leaves stage) grown in an unglazed pot, at the concentration of an active ingredient of 100 ppm. After spraying, the tomato seedling was air-dried at room temperature and a zoosporangium suspension of tomato phytophthora (Phytophthora infestans) was spray-inoculated, and then the tomato seedling was retained in a high-humidity thermostatic chamber (20° C.) maintained at a light or dark state every 12 hours for 4 days. The state of appearance of lesions on leaves was examined and compared with the non-treated tomato seedling and thus the control effect was determined. As a result, the compounds shown below exhibited a preventive value of 80%. The compound numbers correspond to the compound numbers in Table 1.

Compound numbers: 1-17, 1-68 to 1-82, 1-84 to 1-87, 1-131, 1-197, 1-275 to 1-278, 1-323, 1-377, 1-380, 1-399, 1-400, 1-405 to 1-407, 1-415, 1-418, 1-420 to 1-424, 1-429 to 1-431, 1-435, 1-445 to 1-450, 1-452 to 1-460, 1-464, 1-467 to 1-479, 1-481, 1-486, 1-488, and 1-491

INDUSTRIAL APPLICABILITY

The present invention provides a tetrazoyloxime derivative or a salt thereof, which is excellent in a control effect against plant disease injury, and a plant disease controlling agent containing the same as an active ingredient, and is therefore industrially quite useful. 

1. A tetrazoyloxime derivative represented by formula (1):

wherein X represents a halogen atom, a C₁₋₈ alkyl group, a C₁₋₈ alkoxy group, a cyano group, a C₁₋₈ alkylsulfonyl group, a nitro group, a C₁₋₈ haloalkyl group, or an unsubstituted or substituted aryl group; n1 represents any one of integers of 0 to 5, and when n1 is 2 or more, X(s) may be the same or different with each other; A represents a tetrazoyl group represented by formula (2):

(in which Y represents a C₁₋₈ alkyl group), or a tetrazoyl group represented by formula (3):

(in which Y is the same as defined above); and Het represents a pyridyl group represented by formula (4):

(in which R represents a halogen atom, a cyano group, a nitro group, a hydroxyl group, a thiol group, a formyl group, a carboxyl group, an unsubstituted or substituted amino group, an unsubstituted or substituted C₁₋₈ alkyl group, an unsubstituted or substituted C₂₋₈ alkenyl group, an unsubstituted or substituted C₂₋₈ alkynyl group, an unsubstituted or substituted aryl group, an unsubstituted or substituted heterocyclic group, OR¹, S(O)_(m)R¹, COR¹, or CO₂R¹, R¹ represents an unsubstituted or substituted amino group, an unsubstituted or substituted C₁₋₈ alkyl group, an unsubstituted or substituted C₃₋₈ cycloalkyl group, an unsubstituted or substituted C₂₋₈ alkenyl group, an unsubstituted or substituted C₂₋₈ alkynyl group, or an unsubstituted or substituted aryl group, m represents any one of integers of 0 to 2, n2 represents any one of integers of 0 to 3, and when n2 is 2 or more, plural R(s) may be the same or different from each other, when n2 is 0, Z represents a group represented by formula: Q¹C(═O)NH— (in which Q¹ represents a C₁₋₈ haloalkyl group, a C₂₋₈ haloalkenyl group, a C₂₋₈ alkynyl group, a C₂₋₈ haloalkynyl group, a C₁₋₈ haloalkoxy group, a C₂₋₈ alkenyloxy group, a C₂₋₈ haloalkenyloxy group, a C₂₋₈ alkynyloxy group, a C₂₋₈ haloalkynyloxy group, a C₁₋₈ alkoxy group substituted with an alkoxycarbonylamino group, a C₁₋₈ alkoxy group substituted with a C₃₋₈ cycloalkyl group, a C₁₋₈ branched alkoxy group substituted with an unsubstituted aryl group, a C₁₋₈ alkoxy group substituted with substituted aryl, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted heterocyclic group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted C₁₋₈ alkoxy group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted aryloxy group, an C₁₋₈ alkoxy group substituted with an unsubstituted or substituted aralkyloxy group, a C₂₋₈ alkynyloxy group substituted with an unsubstituted or substituted aryl group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted C₁₋₈ alkylthio group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted arylthio group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted C₁₋₈ alkylsulfinyl group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted arylsulfinyl group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted C₁₋₈ alkylsulfonyl group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted arylsulfonyl group, a C₁₋₈ alkoxy group substituted with an amino group which is unsubstituted or substituted with an (unsubstituted or substituted alkyl group), a C₁₋₈ alkoxy group which is substituted with an amino group substituted with an (unsubstituted or substituted aralkyl group), an unsubstituted or substituted aryloxy group, a C₁₋₈ alkyl group substituted with a carboxyl group, a C₁₋₈ alkyl group substituted with an amino group which is unsubstituted or substituted with an (unsubstituted or substituted aralkyl group), a C₁₋₈ alkyl group substituted with an amino group which is substituted with an (unsubstituted or substituted alkyl group), a C₁₋₈ alkyl group substituted with an unsubstituted or substituted aryloxy group, a C₁₋₈ alkyl group substituted with an acyl group, or a C₁₋₈ alkyl group substituted with an unsubstituted or substituted heterocyclicoxy group), when n2 is 1 and R is a halogen atom, Z represents a hydrogen atom, an amino group, or a group represented by formula: Q²C(═O)NH— (in which Q² represents a hydrogen atom, a C₁₋₈ haloalkyl group, a C₂₋₈ alkenyl group, a C₂₋₈ haloalkenyl group, a C₂₋₈ alkynyl group, a C₂₋₈ haloalkynyl group, a C₁₋₈ alkoxy group, a C₁₋₈ haloalkoxy group, a C₂₋₈ alkenyloxy group, a C₂₋₈ haloalkenyloxy group, a C₂₋₈ alkynyloxy group, a C₂₋₈ haloalkynyloxy group, a C₃₋₈ cycloalkyl group, a C₃₋₈ cycloalkyloxy group, a C₁₋₈ alkylamino group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted amino group, a C₁₋₈ alkoxy group substituted with a C₃₋₈ cycloalkyl group, an unsubstituted or substituted aralkyloxy group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted heterocyclic group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted C₁₋₈ alkoxy group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted aryloxy group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted aralkyloxy group, a C₂₋₈ alkynyloxy group substituted with an unsubstituted or substituted aryl group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted C₁₋₈ alkylthio group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted arylthio group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted C₁₋₈ alkylsulfinyl group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted arylsulfinyl group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted C₁₋₈ alkylsulfonyl group, C₁₋₈ alkoxy group substituted with an unsubstituted or substituted arylsulfonyl group, an unsubstituted or substituted aryloxy group, a C₁₋₈ alkyl group substituted with a carboxyl group, a C₁₋₈ alkyl group substituted with an unsubstituted or substituted amino group, a C₁₋₈ alkyl group substituted with an unsubstituted or substituted aryloxy group, a C₁₋₈ alkyl group substituted with an unsubstituted or substituted C₁₋₈ alkylthio group, a C₁₋₈ alkyl group substituted with an unsubstituted or substituted alkoxy group, a C₁₋₈ alkyl group substituted with an acyl group, or a C₁₋₈ alkyl group substituted with an unsubstituted or substituted heterocyclicoxy group), when n2 is 1 or more and at least one R is a cyano group, a nitro group, a hydroxyl group, a thiol group, a formyl group, a carboxyl group, an unsubstituted or substituted amino group, an unsubstituted or substituted C₁₋₈ alkyl group, an unsubstituted or substituted C₂₋₈ alkenyl group, an unsubstituted or substituted C₂₋₈ alkynyl group, an unsubstituted or substituted aryl group, an unsubstituted or substituted heterocyclic group, OR¹, S(O)_(m)R¹, COR¹, or CO₂R¹, or when n2 is 2 or more and at least two R(s) are halogen atoms, Z represents a hydrogen atom, an amino group, or a group represented by formula: Q³C(═O)NH— (in which Q³ represents a hydrogen atom, a C₁₋₈ alkyl group, a C₁₋₈ haloalkyl group, a C₂₋₈ alkenyl group, a C₂₋₈ haloalkenyl group, a C₂₋₈ alkynyl group, a C₂₋₈ haloalkynyl group, a C₁₋₈ alkoxy group, a C₁₋₈ haloalkoxy group, a C₂₋₈ alkenyloxy group, a C₂₋₈ haloalkenyloxy group, a C₂₋₈ alkynyloxy group, a C₂₋₈ haloalkynyloxy group, a C₃₋₈ cycloalkyl group, a C₃₋₈ cycloalkyloxy group, a C₁₋₈ alkylamino group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted amino group, a C₁₋₈ alkoxy group substituted with a C₃₋₈ cycloalkyl group, an unsubstituted or substituted aralkyloxy group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted heterocyclic group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted C₁₋₈ alkoxy group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted aryloxy group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted aralkyloxy group, a C₂₋₈ alkynyloxy group substituted with an unsubstituted or substituted aryl group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted C₁₋₈ alkylthio group, a C₁₋₈ alkoxy group substituted with a substituted or unsubstituted arylthio group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted C₁₋₈ alkylsulfinyl group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted arylsulfinyl group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted C₁₋₈ alkylsulfonyl group, a C₁₋₈ alkoxy group substituted with an unsubstituted or substituted arylsulfonyl group, an unsubstituted or substituted aryloxy group, a C₁₋₈ alkyl group substituted with a carboxyl group, a C₁₋₈ alkyl group substituted with an unsubstituted or substituted amino group, a C₁₋₈ alkyl group substituted with an unsubstituted or substituted aryloxy group, a C₁₋₈ alkyl group substituted with an unsubstituted or substituted C₁₋₈ alkylthio group, a C₁₋₈ alkyl group substituted with an unsubstituted or substituted alkoxy group, an alkyl group substituted with an acyl group, or a C₁₋₈ alkyl group substituted with an unsubstituted or substituted heterocyclicoxy group), or a thiazoyl group represented by formula (5):

(in which R¹¹ represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, a hydroxyl group, a thiol group, a formyl group, a carboxyl group, an unsubstituted or substituted amino group, an unsubstituted or substituted C₁₋₈ alkyl group, an unsubstituted or substituted C₂₋₈ alkenyl group, an unsubstituted or substituted C₂₋₄ alkynyl group, an unsubstituted or substituted aryl group, an unsubstituted or substituted heterocyclic group, OR¹, S(O)_(m)R¹, COR¹, or CO₂R¹, R¹ is the same as defined above, when R¹¹ is a hydrogen atom, Z¹¹ represents a group represented by formula: Q¹C(═O)NH— (in which Q¹ is the same as defined above), when R¹¹ is a halogen atom, Z¹¹ represents a hydrogen atom, an amino group, or a group represented by formula: Q²C(═O)NH— (in which Q² is the same as defined above), and when R¹¹ is a cyano group, a nitro group, a hydroxyl group, a thiol group, a formyl group, a carboxyl group, an unsubstituted or substituted amino group, an unsubstituted or substituted C₁₋₈ alkyl group, an unsubstituted or substituted C₂₋₈ alkenyl group, an unsubstituted or substituted C₂₋₈ alkynyl group, an unsubstituted or substituted aryl group, an unsubstituted or substituted heterocyclic group, OR¹, S(O)_(m)R¹, COR¹, or CO₂R¹, Z¹¹ represents a hydrogen atom, an amino group, or a group represented by formula: Q³C(═O)NH— (in which Q³ is the same as defined above), and a salt thereof.
 2. The tetrazoyloxime derivative according to claim 1, wherein n1 is 0 or X is halogen atom, and a salt thereof.
 3. The tetrazoyloxime derivative according to claim 1, wherein Y is a methyl group, and a salt thereof.
 4. A plant disease controlling agent comprising the tetrazoyloxime derivative according to claim 1 or a salt thereof as an active ingredient.
 5. The tetrazoyloxime derivative according to claim 2, wherein Y is a methyl group, and a salt thereof.
 6. A plant disease controlling agent comprising the tetrazoyloxime derivative according to claim 2 or a salt thereof as an active ingredient.
 7. A plant disease controlling agent comprising the tetrazoyloxime derivative according to claim 3 or a salt thereof as an active ingredient.
 8. A plant disease controlling agent comprising the tetrazoyloxime derivative according to claim 5 or a salt thereof as an active ingredient. 